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Please login to access the full content or check if you have access via8.2.4.1.5.1 Variation 1: α-Elimination (Generation and Reactions of Carbenes, Nitrenes, and Their Precursors)
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Jonczyk, A.; Kowalkowska, A., Science of Synthesis, (2006) 8, 1044.
Reaction of trihalomethanes with sodium hydroxide, a phase-transfer catalyst (usually Q+X−), and alkenes is the simplest and often the most efficient method for synthesis of gem-dihalocyclopropanes (Scheme 48).[3,6,7] The reaction occurs by deprotonation of the trihalomethane by the hydroxide anion at the interphase, resulting in the generation of trihalomethyl anion–sodium cation pairs, which form lipophilic ions via exchange with Q+X−. The latter penetrates into the organic phase and undergoes dissociation into dihalocarbenes and halide anions; the carbene then undergoes stereospecifical addition to the alkene, with formation of the gem-dihalocyclopropane.[3,6,7,13,471–473]
Meeeee 88 Meeeeeeeee ee Meeeeeeeeeeeeee ee Meeee-Meeeeeee Meeeeeeee: Meeeeeeee ee M+M−[8,8,8,88,888–888]
M eeeeeeeeeee eeeeeee ee eeeee-eeeeeeee eeeeeeeee ee eee eeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeee eeeeeeee.[88] Mee eeeeeeee eee eeeeeeeee eeeeee eee eeeeeee eeeee, eeee ee eeeeeee eeeeee eee eeeee (eee eeeeee eeeeeeee eeeeeeeeee ee eeeeeeeeeeeee ee e eeee eeee eeee). Meeee eee eeeeeeee ee e eeeeeee ee ee eeeeee ee e eeeeeeeeee eeee eeeeeee, eee eeeeeeeeee eeeeeeeeee ee eee eeeeeee eeeeee ee ee ee “eeeeee” ee eee M+MM8− eeeeeee. Meeee eeeeeeeeeeeeee eee eeeeeee eeeeeeeeee, eeeee eeeeeeeeee ee eeeeeee eee ee eee eeeeeeee ee eeeeee e eeeeeeeeeeee eeeeeee eeeeeeee ee, ee eeeee, eeeeee eeeeeeeee. Meeeeeeeee ee eeeeeeeeeeeeee eeee eeeeeeeeeeeeeee eee eeeeee eeeeeeeee ee eeee eeeeeeeee ee eeeeeeee eeeeee (Meeeee 88).[888,888] Me eeee eeee, eee eeeeeeeeeeeee, eeeeeeeee eeee eeeeeeeeeeeeee eeeee–eeeeee eeeeee eeeee ee eee eeeeeeeeee, ee eeeeeee eeee eee eeeee, eeeeee ee eeeeeeee eeeee eeeee ee eeeeee eeeeeee ee eee eeeeeee eeeee. Mee eeeee eeee ee eee eeee, eeeeeeeeeeeee eee eeeeeeeeeeeeee eee eeeeeeeeee eee eeeeeeeeeeeee, eeeee ee eee eeeeeee eeeee eeee ee eee eeeeee.[888]
Meeeee 88 Meeeeeeeee ee Meeeeeeeeeeeee ee Meeee-Meeeeeee Meeeeeeee: Meeeeeeee ee Meeeeeee Meeeee[888,888]
Meeeeeeeeeeeee eee eeeeeeeeeeeee eeeeeee; eeeee eeeee-eeeeeeee eeeeeeeee eeeeeeeeee eee eeee eeeeeeee eee eee eeeeeeee eeeeeeeeeeeee, eee eee eeeeeeeeee. Meeeeeeeeeeeee ee eeee eeeeeeee eeee eeeeeeeeeeeeeee, eee eee eeeeee eeeeeeeee eeeeee eeeeeeee eeee eeeeeeeeeeeeeee. Meeee eee eeeeee eeeee-eeeeeeee eeeeeeeee eeeeeeeeeee eeee eeeeee eeeeeeeee, eee eee-eeeeeeeeeeeeeeeeeee (e.e., eeeeeeee[888–888] ee eeeeeee[888–888] 88 eeee 88) eee ee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeeeeee eee eeeeeee eeeeeee (Meeeee 88); eee eeeeeee ee eeeee eeeeeeeeeeeeee eeee eeee eeeeeeee.[8,8,8,88,888–888] Mee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeee eeeeeeeeee ee eeeeeeeee eee eeee eee-eeeeeeeeeeeeeeeeeeeee ee eeee eee eeeeee.[888] Mee eeeeee ee eee-eeeeeeeeeeeeeeeeeeee eee eeeeeeee ee eee eeeeeeee ee e eeeee eeeeee ee eeeeeee[888] ee eeeeeee[888] ee eee eeeeeeee eeeeeee ee ee eeeee e eeeeeeee eeeee ee eee eeeeeeee.[888]
Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee eee-Meeeeeeeeeeeeeeeeee[888–888,888,888]
Mee eeeeeeeee ee eeeeeeeeeeeee-[888] ee eeeeeeeeeeeeeeeeeeee,[888,888] ee eeee ee eeeeeeeeeee- ee eeeeeeeeeeeeeeeeee,[888] eeee eeeeeee ee eee eeeeeeee ee 88% eeeeeee eeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeee eeeeee eeeeeeee ee eee eeeeeeee eee-eeeeeeeeeeeeeeeeeee. Meee eeeeee ee eee ee eeeeeeeeeeeee–eeeeee eeeee eeeeeeeeee, eeeee eeeeeee eeeeeeeee eeeeeeeeeeeee eeeeee, eee eeeee eeeeeeeee eeeeeeee eee eeeeeeeeeeeee.[888–888] Meeee eeeeeeee eeeeeeeeee, eee eeeee-eeeeeeee-eeeeeeeee eeeeeeee ee eeeeeeeeee eeee eeeeee eeeeee, eeeeeeeee eeee eeeeee eeeeeeee,[888] ee eeeeeeeeee eeee eeeeeeeee[888] eeeee eee eee eeeeeeeeeee ee eeeeeeeeeeeeeeeeeee, eeeeeeeeeeeeeeeeeeee,[888] ee eee eeeeee eee eeeeeeeeeeeeeeeeeeee, eeeeeeeeeeee.[888] Meeeeee, eeee eeeeeee-88-eeeee-8,[888] ee eeeee eeeee eeeeee, ee eeee eeeeeeeeeee eeeeeeeeeeeeeeeeeee eeeeeeee[888] eee eeee ee eee eeeeeeeee, eee-eeeeeeeeeeeeeeeeeeeeeeee 88 eee eeeeeeee eeee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeee eeeeeee 88 eeee eeee eeeeeeeeeee (Meeeee 88). Meeeeeee eeee eeeee eeeee-eeeeeeee eeeeeeeee, eee eeee ee eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeee eeeee ee eeee eee.[888]
Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee eee-Meeeeeeeeeeeeeeeeeeeeeee[888]
Mee eeeeeeee eeeeeeee ee 8 eeeeeeeeeee ee eeeeeeeeeeeeeee ee eeeeeeeeee eeeeee[888,888–888] ee eeeeeee eee eeee ee eeeeee ee eeeeeeeeeeeeeeee eee eeeeeeee ee eeeeeeeeee,[888] ee ee e eee-eeee eeeeeeeee,[888] eeeeeee eee eeeeee eeee ee eee eeeeeeeeee ee eeeeeeeeeee (Meeeee 88). Me eeeee eeeeeeeee e eeeeeeeeeeeee eeeee,[888,888,888] ee eeeeee[888,888] ee- eee eeeeeeee, eee ee eee eeeeee eeeee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeeeee, eeeeee eeeeeeeeeeeeeeeeeee eeeeeeee,[888] ee e eeeeeeeee eeeeeeeeee eeeeeeee eeee,[888] ee eeee ee eee eeeeeeee. Me eeee eeeee, eeeeeeeeeeee ee eeeeeee. Meeeeee ee eeeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeee,[888] eeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeeee,[888] eeeeeeeeeee eeeeeeeeeeeeeeee,[888] ee eeeeeeeeee[888] eeeeeee eeeeeeeeeeeee eee, eeeee, eeeeeee eeeeeee eeeeeeeee. Me eee eeeee eeee, eeeeeee ee eeeeeeeeeeee,[888,888] eeeeee eeeeeeeeeeee,[888] ee eee-eeeeee ee eeeeeeeeeeeeeee[888,888] eee eeeeee eeeeeeee. Me e eeee, eeeeeee eeee eeeeeeee eeeeeee eeee eeeeeeeeeeeeee, e.e. eee eeeeeeee eeeeeeeeeee eeee 8,8-eeeeee-eeeeeeeeeee eeeeeee eeeeeee eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee.[888]
Meeeee 88 Meeeeeee ee Meeeeeeeeeeeee ee Meeeee[888]
Mee eeeeeee ee eeeeeeeee ee eeeeeee 88 eee 88, eeeeeeeeeee eeee eeeeeeee-eeeeeeeeeee eeeeee, (eeeee,[888–888] eeeeeeeeeeeeee,[88,888–888,888–888] eeeeeeee,[888,888,888,888,888] eeeeeeee[888,888]) eeee eeeeeeeee (eeeeeee eeeeeeeeee) eeeeee eeee Meeeeee eeeeeee 88 ee eee eeeeeeeeeeeee eeeee eee eeeeeeeee eeeeeee eeee eeeeeeee 88 ee eeeeeeeeeeeee eeeeeeeeeeeee, ee eeeeee ee eee eeee ee eeeeeeee[888,888] eee eeeeee (Meeeee 88).[888,888,888,888,888] Mee eeeeeeeee ee eee eeeeeeeeeeeee eeeeee, eee eeeeee ee eee eeeeeee,[888] eee, eeeee, eee eeeeeeeee ee eee eeeeeeee,[88,888,888,888] eeee eeeeeeeee eeeee ee eeeee eeeeeeeee. Me eee eeee ee eeeee eeeeeeeee, eeeeeee eeeeeeeeeeeeeee ee eee eeeeeeeeeeee eeeee.[888,888,888] Meeeeeee eeee eeeeee, eeee eeeeeee eeee eeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeee, eeeeee eee eeeeeeee ee eeeeee eeeeeeee ee eee eeeeeeeeeeeeeee eeeee ee M8 ee eee eeeee eeeee[888] (eee Meeeeee 8.8.8.8.8.8), eeeee eeeee eeeeeeeeeeeeeeeeeee eeeeeeee eeeeeee, eeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeee.[888] Meee eeee eeeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeee, eee eeeeee eeeeeee eeeee eeeee ee eee eeee ee eeeeee-eeeeeee eeee eeeeee[888] eee 8-eeeee-8M-eeeee-8-eeee.[888] Meeeeeeeeeeeee, eeeeeeeee ee eeeee-eeeeeeee eeeeeeeee, eeeeeee eeeeeee eeeeee eeeeeeee ee eeeee eeeeee, eeeeeeee,[888] eeeeeee, eeeeeeee, α-eeeeeeeeeeeeee[888] (eee eee eeeeeeeeeeeee,[888] ee ee-, eee-, ee eeeeeeeeeeeeeeeeee), ee eeee ee eeeee eeee e eeeeee eeeeeeeeeeeee.[888,888]
Meeeee 88 Meeeeeee ee Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee Meeeeeeeee eeee Meeeeeeeeeeee Meeeeee[888,888,888]
Mee eeeeeeee eeeeeeeee eeeeeee eee eeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeee eeee eeeeeee eeeeeeee:[888,888] eee eeeee ee eeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeee eeeee eeeeeeeeeeee eeeeee eeee 88:8 ee 8:88.[888]
M—M eeeee eeee eee eeeeeee, eeeeeeee, eeeeeeeee, eeeeeeee, ee eeee ee eeeeee eee eeeeeee eeeeeeeee eeeeeeeee eeee eeeee-eeeeeeee eeeeeeeee eeeeeeeee eeeeeeeeeeeeee.[888–888] Meeeee eeeeeeeee ee eeeeeeeeeeeeeee ee eeeeeeee eeee 8,8-eeeeeeeeeeeeeeeeeeeeeee.[888] Mee eeeee ee eeeeeeee- eee eeeeeeeeeeeeee eeeeeeeee eeeeeeee ee eeeeeee eeeeeeee (eeeeeeee e eeee eeeee ee eee eeee ee 8,8,8-eeeeeeeeeeeeee 8,8-eeeeeeeeee ee eeeeeeee[888]), eee eeee eeeeeeee eee eeeeeee eeeeee eeeeeeee ee eeeeeeeeeeee. 8-(Meeeeeeeeeeeee)eeeeeeeeee 88 eee eeee eee eee eeeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeee (Meeeee 88).[888] Mee eeee eeeeeee, eeeeeeeee ee eeeeeeeeeeeeeee eee eeeeeee eeee eeeeeeeeeeeee.[888] Meeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eeee eeeeee- ee eeee-eeeeeeeeeeeeeeeeee-eeeeeeeee eeeeee eeeeeeeee eeeeeeee eee eeeeeeeee-eeeeeeeee eeeeee eeeee ee eeeee.[888]
Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee Meeeeeeeeeeeeee eeee 8,8-Meeeeeeeee[888]
Meee eee eeeeeeeee eeeeeeee eeeeee, eeeeee, ee eeeeeeee, eee eeeeeeee eeee eee eeeeeeeeeeeee eeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeee, eeeee eeee eeeeeeeee eeeeeee eeeeeeeeeeeeeee. Meee, eeeeeeee (eeeeeee, 8,8,8-eeeeeeeeeeeeeeee) eeee eeeeeeeeeeeee ee eeeeee ee ee. 88% eeee eeeeeeeeeeeeeeee eeeee eeeee-eeeeeeee-eeeeeeeee eeeeeeeeee,[888] eee eee eeeeeee eeeeeee ee eeeeee eeeeeeeeeee.[888,888] Meeee-eeeeeeee-eeeeeeeee eeeeeeeee ee eeeeeeeeee eeee eeeeeee eeeeee 88 eeee ee eee eeeeeeeee ee eeeeeeeeeee 88,[888,888] eeeee eeee eeeeeeeee eeeeee 88 eee M,M-eeeeeeeeeeeee eeeeeeeeee 88 eee eeeeeeee (Meeeee 88).[888,888] Meee eee eeeeee eeee ee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeee, eee eeeeeeeeeeeeeeee eeeeeee.[888] Meeeeeeeeeeeeee ee eeeeeeee eeeeeeee ee eee eeeeeeeeeee ee eeeeee,[888,888] eeeeeeeeee, eeeeeeeee, eee eeeee.[888] Meeeee eeeeee eeeeeeeee eeee eee eeeeeeeee ee eeeee eeeeeeee eeee eeeeeeeeeeeeeee eeee eeeeeeee ee e 8,8-eeeeeeeeeee eeeeeeeeeeeee, eeeee eeeeeee eeeeeeeeee eeee eeeeeeeeeeeeee ee eeee eeeeeee eeeeeeeee eeeeee.[888]
Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee Meeeee eeee Meeeeeeeee[888,888]
Mee-eeeeeeeeeee eeeee-eeeeeeee-eeeeeeeee eeeeeeeee ee eeeeeeeeee eeee eeeeeeee eeeeeeeee eeee ee 8,8,8-eeeeeeeeeeeeeeeee (eee eeeeeeee ee eee eeeeeeeeeeeeeee eeeee ee eee eeeeeeee eeeeee), eeeee eee ee M-eeeeeeeeee eeee eeeeeeee eeeeeee.[888] Me eee eeee ee eeeeeeeeeeeeeeeeeeeee, eee eeeee–eeeeee eeeeee eeeee eeeeee eeeeeee eeee eee eeeeee–eeeeee eee.[888] Mee eeeeeeeeeeeeeeeee ee eeeeeeee eeee eee eeeeeee ee eeeeeee eee ee eee eeeeeeee ee M-eeeeee Meeeeeee eeeeeeeee.[888,888] Me e eeeeee eeeee ee eeeeeeeeeeee (88±8°M), eeeeeeeeee eeeeeee α-eeeeeeeeeeee eeeeeeeeee eeeee[888] ee eeeeeeee eeeee[888] ee eeeeee ee 88–88%, ee eeeeeeeee eeee eeeeeee[888] ee eeeeeeee eeeeeeeee.[888] Meeeeeeeeeeeeeeeeeeee ee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeee (eeeeeeeeee) eeeee eee eeeeeeeeee eeeeeee eeeeeeeeee eeeee ee eeeeee ee 88–88%.[888] Mee eeeee-eeeeeeee-eeeeeeeee eeeeeeee ee eeeeeeeeee eeee eeeeeeeeeeeee ee 88°M eeeee 8-eeeeeeeeeeeeeeeeeeeeeeeeeee eeee, eeeee ee 88–88°M, e eeeeeee eeee eeeeeeeeee eee eeeeeeeeeeeee α-eeeeeee eeee ee eeeeeeee.[888,888] Meeeeeeeeeeeeeee eee eeeeeeee eeeeeeee ee eeee eeeeeee.[888,888,888,888] Meeee- ee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeeeee eeeee ee eee eeeeeeeee ee eeeeeeee α-eeeee eeeeee,[888] eeeeeeee eeeeeeeeeeee,[888–888] (e.e., 88 eee 88) (Meeeee 88),[888] ee eeeeee.[888]
Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeeee[888]
Mee eeeeeeeeeeeee eeeeeeeeee ee eeeeeeeeeeeeeee eee eeee eeeeeee ee eee eeeeeeeee eeee eeeeeeeeee, eeeeeee ee eee eeeeeeeee ee 8- eee 8-eeeeeeeeeeeeeeeeeeee (Meeeee–Meeeeee eeeeeeee[888,888]). Meeeeeeee ee eeeeeeeeee eeee eeeeeee eee eeeeeee eeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeee eeeeeee e eeeeeeee, eee eeeeeeeee ee eeeeeeee eeeeee eeeeeee eeeeeeee eee eeeee ee eeeeeee ee eee eeeeeeee eeeeeeeee eeeeeeeeeeeeeee.[888] 8,8,8-Meeeeeeeeeeeee eeeeeee eeeeeee eeeeeeee eeee eeeeeeeee, eeeee eeeee-eeeeeeee eeeeeeeee eeeeeeeeee, ee eeee eee eeeeeeee eeeeeeeeeeee-eeeeeeeeeee eeeeeeeeeee;[888,888] eee eeee eeeeeee eee eeeeeeee ee eee eeeeeeeeeee ee eeeee-eeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeee.[888] Meeeeeeee ee eeeeeee eeee α- ee β-eeeeeeeeeeee eeee ee eee eeeeeeeee ee eeee-eeeeee eeeeeee eeee, eeeeeee eee eeeee eeeeeeeee ee eee eeeeeeeee eeeeeee eee eee eeeeeeeee eee eee eeeeeeee eeee eeeeeee.[888]
Meeeee(eeeeeeeeeeeeee)-,[888] eeeeee(eeeeeeeeeeeeee)-,[888] eee (eeeeeeeeeeeeee)eeeeeeee,[888] eeeeeeeee ee eee eeeee-eeeeeeee eeeeeeeee eeeeeeeeee (88% eeeeeee eeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee) eeee eeeeeeeeeeeeee eeeeee, eeeeeeeeeeeeee eeeeee, eee eeeeeeeeeeee eeeeee eeeeeeee, eeeeeeeeeeee, eeeeeee eeeeeeee ee eeeeeee 88 (Meeeee 88). Meeeeeeee, eeeeeeeeeeeeee eeeeee eeeee eeeee eee eeeeeeeeeeee eeeeee(eeeeeee)eeeeeee eeeee eeeeeeeee eeeeeeee ee eeeeeeee, eeeeeeeee eeeeeeeeeeeee ee eee eeeeee (8–88%).[888]
Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee Meeeee-Meeeeeeeeee Meeeeeeeeeeee[888,888]
Meeeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeee-[888–888] (eeee M-eeeeeeeeeeeeeeeeeeeee ee eeeee M-eeeeeee eeeeee) eee eeeeeeeeeeeeeeeeeeee[888,888] ee eeeeeee 88 ee eeeeeeee eeeee eeeeeeeeee ee eeeee-eeeeeeee eeeeeeeee (Meeeee 88). Mee eeeeeeeeee ee eee eeeeee eeeeeee, eeee eeeeeeeee eee eeeeeee eeeeeee eee eeee.
Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeee ee (Meeeeeeeeeeeeeeeee)eeeeeeeeeeeee[888]
Mee eeeeeeeee ee eeeeeeee, eeeeeeeee eeeee eeeeeeeee ee eeeee-eeeeeeee eeeeeeeee, eeee eeeeeeeeeeee eeeeeeeee eeee eeee eeeeeeee.[888] Meeeeeeee eeee eee eeee ee eeeeeee eee eee eeeeeeeee ee eee eeeeeeeeeee, eeeeeee eeeeeeee eeeeee, e.e. ee eee eeee ee eeee-eeeeeeee eeeeeeeeeeee (eeeeeee, eeeeeeeeee, eeeeeeeeeeee) ee eeeeeeeeeeee, eeeeeeeeeeeee eee eeee eeee eeeeeeeee eee/ee eeeeeeeee ee eeeeeeeeeeeeee ee eeeeeeee.[888]
Meeeeeeeeeeeeeeeeeeee, eeeeeeeee eeee eee eeeeeeee ee M-(eeeeeeee)eeeeeeee eeeee eeeeeee eeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeee eeeeeee, eeeee M-(eeeeeeeeeeeeee)eeeeeee (88%), eeeee eeeeeeee eeeeee-M-(eeeeeeeeeeeeee)eeeeeeee (eeeee 88%), ee eeeeeeeeeeeeeeeeee (88%) ee eeeeeeeee eeee eeeeeee, eeeeeee, ee eeeeeeeeeee, eeeeeeeeeeee.[888] Meeee ee eee eeee eeeeeee ee eeeeeee eeeeeeeeee, eeeeeeeeeeeeeeeeeeeee ee eeeeeee eeeeeeeee ee eeeee-eeeeeeee eeeeeeeee eeeee eeee eeeee (e.e., eeeeee eeeeeeeeeee).
Meeeeeeeeeee Meeeeeeee
eeeee-8,8-Meeeeeee-8,8-eeeeeeeeeeeeeeeeeeee (88, M8 = M8 = Me; M8 = M8 = M; M = Me); Meeeeee Meeeeeeee:[888]
Me e eeee ee (M)-eeeeeeee (8.8 e, 8.8 eeee) ee MMMe8 (88.8 e, 8.88 eee) eee eeeee MMMMM (888 ee) eee e eeee eeee ee 88% ee MeMM (88.8 eM). Mee eeeeeee eee eeeeeee eee 88 e, ee eeeee eeee eeeeeee, eeee ee ee, eeeeee eeee M8M, eee eeeeee eeee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eeee MMMe8, eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeee eee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee; eeeee: 8.88 e (88%); ee 888°M/8.888 Meee; ee 88°M.
Meeee 8,8,8-Meeeeeeeeeeeeeeeee (88, M8 = M; M8 = MM8Me); Meeeeee Meeeeeeee:[888]
Me e eeeeeeeeee eeeeeee eeeeeee ee eeeee eeeeeeee (88.8 e, 8.8 eee), MMMe8 (88.8 e, 8.8 eee), MMMMM (8.88 e, 8 eeee), eee eeeeeee (88 eM), 88% ee MeMM (88 eM, 8.88 eee) eee eeeee eeeeeeee ee 88°M. Mee eeeeeeee eee eeeeeee ee 88°M eee 8 e, eeeeee, eeeeeee eeee M8M (888 eM) eee MMMe8 (88 eM), eee eee eeeee eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeee eeee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eeee MMMe8 (8 × 88 eM), eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee 8% ee MMe (88 eM) eee eeee M8M (888 eM). Mee eeeeeeee eeee eeeee (MeMM8), eee eeeeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88.8 e (88%); ee 88–88°M/8.88 Meee.
References
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| [482] | Meeeeeeeee, M.; Meeee, M.; Müeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [483] | Meeeeee, M. M.; Meeeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 888. |
| [484] | Meeeeee, M. M.; Meeeeeeee, M., Meeeeee Mee. Meee., (8888), 8888. |
| [485] | Meeeeee, M. M.; Meeee, M., Meee. Mee., (8888) 888, 8888. |
| [486] | Meeeeee, M. M.; Meüeeee, M., Meeeeee Mee. Meee., (8888), 888. |
| [487] | Meeeeeńeee, M.; Meełeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Mąeeeee, M., Meeee. Meeeee., (8888) 8, 888. |
| [488] | Meeeeeńeee, M., Meeeeeeee, (8888), 888. |
| [489] | Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
| [490] | Meee, M.; Meeeeeeee, M.; Meeeeeeeee, M., Meee. Mee., (8888) 888, 8888. |
| [491] | Meeeeeeee, M.; Meeeeeeøe, M., Meeee. Meeeee., (8888) 88, 8888. |
| [492] | Meeeeeee, M. M.; Meeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 88888e. |
| [493] | Meeeeee, M. M.; Meeeeee, M., M. Meee. Mee., Meeee., (8888), 888. |
| [494] | Meeeeeeeeeee, M. M.; Meee, M.-M., Meeee. Meeeee., (8888) 88, 8888. |
| [495] | Meeeee, M. M.; Meeee, M.; Meeeeee, M. M., Meee. Meee., (8888), 888. |
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| [497] | Meeeeeeeeee, M. M.; Meeeeeeee, M. M.; Meee, M. M.; Mee'eee, M. M.; Meeeeeee, M. M., Meee. Meee. Meee., (8888) 88, 8888. |
| [498] | Meeeeee, M.; Meeeeeć, M.; Meeee, M.; Meečee, M., M. Mee. Meee., (8888) 88, 8888. |
| [499] | Meeee, M.; Meeee, M.; Meeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [500] | Mąeeeee, M.; Meeee, M., Meee. Meee. Mee. Mee., Mee. Mee. Meee., (8888) 88, 88; Meee. Meeee., (8888) 88, 888888e. |
| [501] | Meeeeee, M. M., Meeeeee Mee. Meee., (8888) 888, 888. |
| [502] | Meeeeeńeee, M.; Meółeeeeee, M.; Meńeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [503] | Meeeee, M.; Meeee, M.; Meeee, M.; Meeee, M., Meee. Meee. Mee. Mee., (8888) 88, 888. |
| [504] | Meeeeee, M. M.; Möeee, M., Meee. Mee., (8888) 888, 8888. |
| [505] | Meeeee, M. M., Meee Meee. Meeee., Mee. M, (8888) 88, 888. |
| [506] | Meeeeee, M. M.; Meeeeeeee, M., Meee. Mee., (8888) 888, 888. |
| [507] | Meeeee, M.; Meee, M.; Meeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [508] | Meeeeeńeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [509] | Meeeeeńeee, M.; Młeżeeeeee, M.; Mąeeeee, M., Mee. M. Meee., (8888) 88, 888. |
| [510] | Me Meeeeee, M.; Meeeee, M.; Meeeee, M. M.; Meeee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
| [511] | Meeee, M. M.; Meeeee, M. M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [512] | Meeeeeeee, M. M.; Meeeeee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
| [513] | Meeeeeńeee, M.; Meeeeee-Meeeee, M.; Meeee, M.; Meńeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [514] | Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. Me.; Meeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meeee., (8888) 888, 888888e. |
| [515] | Meeee, M.; Meeee, M. M. M.; Müee-Meeeeeeeeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 8888. |
| [516] | Meeee, M. M.; Meeeee, M. M. M.; Meeeee, M. M. M.; Meeeee, M. M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [517] | Meeeeee, M. M.; Meeeeeeee, M., Meeeeee Mee. Meee., (8888), 888. |
| [518] | Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [519] | Mąeeeee, M.; Meeeeeńeee, M., Meee. Meee., (8888) 88, 888; Meee. Meeee., (8888) 88, 888888e. |
| [520] | Mee, M. M., M. Meee. Meee., (8888) 88, 888. |
| [521] | Meeeeeeee, M., Meee. Mee., (8888) 888, 8888. |
| [522] | Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [523] | Meeeeeeee, M., M. Meee. Mee., Meeee., (8888), 88. |
| [524] | Meeeee, M.; Meeeeee, M.; Meeee, M., Meee. Meee., (8888), 8888. |
| [525] | Mąeeeee, M.; Meeeee, M.; Meeeeeńeee, M., Meee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 88888e. |
| [526] | Meeeeee, M. M.; Meeeeee, M., M. Meeeeeeeeee., M, (8888) 88, 888. |
| [527] | Meeee, M. M.; Meeee, M. M.; Mee, M. M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [528] | Meeee, M. M.; Meeeee, M. M.; Meeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [529] | Mąeeeee, M.; Meeeeeeeee, M., Meee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 88888e. |
| [530] | Mee'eeeee, Me. Me.; Meeeeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 88888e. |
| [531] | Meeeee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [532] | Möeee, M., M. Meeeeeeeeee., M, (8888) 88, 888. |
| [533] | Meeeeee, M.; Meeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [534] | Meee, M.; Meeeeeee, M., Meee. Mee., (8888) 888, 88. |
| [535] | Meeee, M. M.; Meeeeeee, Me. Me.; Meeeeeee, M. M.; Meeeeeeeeee, M. M., Meee. Meeeeeeeeee. Meeeee., (8888), 88; Meee. Meeee., (8888) 888, 88888e. |
| [536] | Meeeá, M.; Meeeeeeee, M., Meeeeeee, (8888) 88, 888. |
| [537] | Meee, M., Meeeeeeee, (8888), 888. |
| [538] | Meeeeee, M. M.; Meeeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888. |
| [539] | Meee, M.; Müeeeeäee, M.; Meeeee, M., Meeeeeeee, (8888), 888. |
| [540] | Meee, M.; Müeeeeäee, M.; Meeeee, M., Meeeeeeee, (8888), 888. |
| [541] | Meeeeee, M.; Meeeeee, M.; Meeeeš, M., Meee. Meee. Meee, (8888) 88, 8888. |
| [542] | Mee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [543] | Meee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [544] | Mee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [545] | Mee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [546] | Mee, M. M., Meeeeeeee, (8888), 88. |
| [547] | Mee, M. M., Meeeeeeee, (8888), 88. |
| [548] | Mee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [549] | Meeeeee, M.; Meeeee, M. M., Mee. Meeee. (M. M.), (8888) 88, 8. |
| [550] | Meeeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
| [551] | Meeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [552] | Meeeee, M.; Meeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [553] | Meeeeee, M.; Meeeee, M. M. M.; Meeee, M.; Meeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [554] | Meeeeeee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [555] | Mąeeeee, M.; Meełeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [556] | Meee, M. M.; Meeeeeeeee, M. M., Meeeeeeee, (8888), 888. |
| [557] | Meeee, M.; Meeeeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [558] | Meüee, M.; Müee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [559] | Meeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [560] | Meeeee, M. M.; Meeeee Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [561] | Meeeee, M. M.; Meeeee Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [562] | Meeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [563] | Mee, M. M.; Meeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [564] | Meeeeeee, M. M.; Meeeeeeeee, M. M., Meee. Meeeeeeeeee. Meeeee., (8888), 8888; Meee. Meeee., (8888) 88, 88888e. |
| [565] | Meeeeee, M. M.; Meeeee, M., Meeeeee Mee. Meee., (8888), 8888. |
| [566] | Meeeee, M.; Meeeeeee, M.; Meeeee, M., Meee. Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
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