Science of Synthesis

de Meijere, A.; Kozhushkov, S. I., Science of Synthesis, (2009) 48, 540.

Cyclopropanations of alkenes with arylcarbenes (arylcarbenoids) can be achieved in essentially the same ways as discussed above for cyclopropanations with methylene (see Sections ‌48.2.1.4.1‌–‌48.2.1.4.4‌; several of these reactions are also discussed in part in Section ‌48.2.1.4.1‌). However, in contrast to those with diazomethane, the great majority of such cycloadditions of arylcarbenes are initiated by photochemical or thermal decomposition of aryldiazomethanes (‌Scheme 63‌, route a). Other examples deal with two-step cyclopropanations by cycloaddition of an arylhalocarbene (routes d and f) (see Houben–Weyl, Vol. E 19b, p 981) and subsequent reductive removal of the halogen (route e). Only a few examples of carbenoid cycloadditions (route b) and of catalytic decompositions of (di)aryldiazomethanes in the presence of alkenes (route c) are known (see Houben–Weyl, Vol. 4/3, pp 101, 257, and Vol. E 17a, p 326). All of these methods have their disadvantages. For example, the highly reactive (di)arylcarbenes produced photochemically or thermally (routes a and d) react in their triplet states and thus (1) not stereospecifically[‌300‌,‌301‌] and (2) with hydrogen abstraction as a major side reaction. Therefore, the yields of cyclopropanes ‌196‌ are moderate, even if the alkene is used as a solvent; otherwise the yields are low and the cyclopropanes ‌196‌ are contaminated with a number of byproducts. In the case of unsymmetrically substituted carbenes and carbenoids (routes a–f), mixtures of cis- and trans- (syn- and anti-) diastereomers in different proportions are normally formed. Therefore, these methods are of synthetic value only when the symmetry and substitution pattern of the alkene predetermine the formation of only one isomer of ‌196‌.

‌Meeeee 88‌ Meeeeeeee Meeee ee Meeeeeeeeeeeeeee ee ee Meeeee eeee (Me)eeeeeeeeeeee ee Meeeeeeeeeeeeeee

Meee eeeeeeeeeeeeeeeee ee eeeeeee eeee (ee)eeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeeee (eeee eeeeeeeeee eeeeeeeee) eeee eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeee ‌888‌ eee eeeeeeeeee ee ‌Meeee 8‌ (eeeeee eeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee eee eeeeeee eeee eeee eeeeeeee).[‌888‌,‌888‌–‌888‌] Me eeeee ee eeeeeeee eeeeee ee eee eeeeeeee ‌888‌, eeeee eeeeeeeeee eeeee eeeeeeeeee eee eeee eeeeeeeeee eeeeeeeeeeee ee eeeee eeeeeeeee-eeeeeeeeeee eeeeeeeeeeeee eeee eee ee eeeeeeee ee eeeeeeeeeeeeeeeee (eeeeeee 8, 8, 88–88). Me eeeeeee 8 eee 8 eee eeeeeeeeeeee ee eeeeeeee ee eee eeee eeeeeee, eee ee eeeee 8 ee e eeeeeeeee ee e eeeeeee eeeeeee eeeee eee ee eeeeeeeee ee eeeeeeeeeee MM eeee.[‌888‌]

‌Meeee 8‌ Meeeeeeee ee (Meeee)eeee-eeeeeeeeeee Meeeeeeeeeeee ee Meeeeeeeeeeeee ee (Me)eeeeeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeee eee Meeeeeeeeeeeeeeeeee[‌888‌,‌888‌–‌888‌]

e Meeee (eeee/eee) = 8.8.

e Meeee (eeee/eee) = 8.8.

e Meeee eee eeeeeeee.

Mee eeeeeeeeeeeeeeeee ee eee eeeeeeeeeeeeee ee eeeeeeeeeeeeee eee ee eeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeee eeee eeeeeeeeeeeee eeeeee eeeeeeee, eeeee eee eeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeeee, e.e. ‌888‌, eeee eeee(8-eeeee)eeeeeee eeeeeeeeeeeeeeeeeeee (‌Meeeee 88‌). Meee eeeeeeeeeeeee eeeeee eeeeeeee eeeeeeee ee eeeeeee eeeeeeeeeeeeeeeeee ee eeee eeeeeeeeeeeeeeeeeee ‌888‌ ee eeeeee eeee eeeeee. Meeeeeeeeeeee, eeeee eeeeeeeeeeee eeee eeee eeeeeeeee ee e eeee eeeee eeeee, eee ee eeeeeeee eeeeeeeeeeee eeeeeeeee eee eeee eeeeeeee.[‌888‌] M eeee eeeeeeeeeee eeeeeeeeeeeeee, ee eeeee e eeeeeeeeeeeeeee ‌888‌ eeeeee eeee eeeeeeeee-8,8-eeeee eeeeeeeeeee ee e eeeeeeeee eeeeeeeeee ee e eee(eeeeeeeeeee) ‌888‌ ee eeee e 8,8-eeeeee-eeeeeeeeeee eeeeeeeeee[8.8.8.88,8.88,8]eeeeee (eeeeeeeeeeeeeeeee) ‌888‌,[‌888‌] eeeee eeee ee ee eeeee eee ee eee eeee eeeeee ee ‌888‌ ee eeeeee e (eeeeeeeee)eeeeeee ee e eeeeeeeee eeeeee (‌Meeeee 88‌). Mee eeeeeeeee eeee eeeeeee eeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeeee ‌888‌ eeee eee eeee-eeeeeeeee eeeeeeeeeeeeeeeee ‌888‌ eeeee eeeeeeeee eeee eeeeee M-eeeeeeeeeeee eeeeeee eeeeeeeee ee eeee(M) ee eeee eeeeeeee(MM) eeeeeeee eeeeeee ee ee eeee eeeeeeeee; eeeeeee, eeee eeeeeeee ee eeeee eeee eee ‌888‌ eeee e eeeeeeeeeeee eeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeee Meeeeeeeeeeee ee 8,8-Me-8-eeeeeeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

‌Meeeee 88‌ Meeeeeeeeeeeeee ee Meeeeeeeeeeee Meeeeee Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeeeeeeee eeee eeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeee eeee Me8MM8M ee Me8MMM8 eeee eeeeeeeee eeee eeeeeeeeeeee eeeeeeee ee eeeeeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeee (‌Meeeee 88‌, eeeee e) eee eee eeeeeeee eee eeeeeeee eeeeee eeee.[‌888‌,‌888‌] Meeeeee, eee eeeeeeee ee eeee eeee ee eeeeeeeeeeeeeeee eee eeeee eeee e eeeeeeeeeee eeeee. Mee eeeee eee ee eeee eee eee ee eeeeee(eeeeee)eeeeeee eeeeeee ee eeeeeeeeeeeee ee Meeeeeee'e eeeeeeeeeeee ee eee Meeeeee–Meeee eeeeeeeeeeeeeeee ee eeeeeeeeeee (‌Meeeee 88‌).[‌888‌] Meee eeeeeeeeeeeeee eee eeee eeeeeeee e eeeeeeeeee eeee eeeee, eee eeee eeeeee eeee ee eeeeeeeeeeee eeee eeeeee ee eeeeeeeeeeeeeeeee. Mee eeeeee eeeeeee ee e eeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee ‌888‌, eeeeeeeee eeeeee eeee (eeeeeeeeeeeeee)eeeeeee (‌888‌) eee eeeeeeeeeeeee, eeee eee eee eeeeeeeeeeeeeeeeeeeee ‌888‌ ee eeeeeeeee eeee eee eeee eeeeeeeeee ee eeeeeeeeeeeee.[‌888‌] Meeeeeeeeeeee ee ‌888‌ eeee eeeeeee eeeeeeeee eeeeeeeeeeeee ‌888‌ ee eeee eeeeee eee ee eeeeeeee ee eeeeeeeeeeeee, eeeee ee e eeeeee eeeeeeee eee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeee (eee eeeee). ‌Meeeee 88‌ eeeeeeeeee eeeee eeeeeeee eeee eeeeeeee eee eeeeeeeeeeee eeeeeee ee eee eeeeee eeeeeeeeeeee eee eeeeeeeee ee eeee eee eeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeeeeee eeee Meeeee- eee Meeeeeeeeeeeeeeeeeeeee Meeeeeeee eeeee Meeeeeeee Meeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeeeeeee eeee eeee eeeeeeeeee (ee eeeeeee eeeeeeeeee), eeeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeeeeee ‌888‌ eeee 8 eeeeeeeeee ee e eeee(MM) eeeeee (ee e eeeeeee eeeeee),[‌888‌] eeeeeeee eeeeeeeeeeeeeeeee ‌888‌ ee eeeeee eeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeeee ee ‌888‌ ee eee eeeeeeee ee eeeeeee (‌Meeeee 88‌; ee. ‌Meeee 8‌); eeeeeee, eeeeeeeeeeeeeeeeeee eeeeeee eeeee eeeeee eeeee eeeee eeeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeeee eeee Meeeee- eee Meeeeeeeeeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeeee eeee Meeeeeeee eeee Meee(MM) Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeee eeeeeeeeeeeeee eeee eeee eeeeeee ee eeeeeeeeeeeeeeeee ee eeeeeee eeee eeeeeeeee eeeee eeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeee eeeee eeeeeeeeee-eeeee eeeeeeeee. Me eeee eeeeeee, e eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeeeeeeeeeeeeee ee 8-eeeeeeeeeeeeeeeeeee (‌888‌) ee eee eeeeee ee eee eeeeeeee eee eeee eeeeeeee, ee eeee eeeeee eeeeeeee eeeeee ‌888‌ ee ‌888‌. Meee eee eeeeeeeeee ee eee eeeeee ee eeeeee eeeeeeeeeee ee eee eeeeeeeeee eeeee ee eeeee ee 8888 (‌Meeeee 88‌; eeeeee eee eeeeeeeeee eeee eee eeee eeeeeeee).[‌888‌] Mee eeeeeeeee eeeeeeeeee ee e eeeee eeeeeee ee eeeee eeeeeeeee ‌888‌–‌888‌ ee eeee eeeeeeeeeeeeeeee eeee eeee eeeeee, ee eeeeeeeeee ee ‌Meeeee 88‌.[‌888‌–‌888‌] Meeeeee, eeeee eeeeeee eee eee eeee eeeee eeeeeeeee eeeeeeeeee, eee eeeee eeeeeeeee eeeeeee eeee eee eeee eeeeeeeeee ee eeee ee, eee eeeeeee, eee eeeeeeeeeeeeeeeee ee eeeeeee eeee eeeeeeeeeeee eeeee eeeeeeeee(MM) eeeeeee eeeeeeeee. Meee, eee eeeeeee eeeeeee ‌888‌ eeeeeeee ee eeeeeeeee eeeee ee eee eeeeeeeeeeeeeeee ee eeeeee, eee eeee eeeeeee (‌888‌, M8 = Me) eee eeee eeeeeeee ‌888‌ eeeeeeeee e eeeeeee eeeeeee ee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeeee eeee Meeeeeeee Meeee Meeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeeeeeee eeeee Meeeeeeeee Meeee Meeeeeeee[‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeeeeeeee eee eeee ee eeeeeeee ee eeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeee (‌Meeeee 88‌, eeeee e), eeeee, ee eeee, eee eeeeeeee ee (8) eeeeeeeeeeeeeeee ee eeeeeee eeee eeeeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeeeeee ee eeeeeeeeee (eeeee e, eeee eeeeeeeeee eeee[‌888‌,‌888‌]) (‌Meeeee 88‌) ee (8) eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeeeee eeee (eeeeeeeeeeee)eeeeee eeeeeeeeeee eeeeeeeee ee Meeeeee'e eeeeeeee (eeeee e, eeee eeeeeeee eeee) (‌Meeeee 88‌).[‌888‌–‌888‌] Meee eee eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeee, eee eeeeee eeeeeeee ee eeeeeee eeeeeeeeeeeeeeeeee (e.e., eeee eeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeee), eee eee eeeeeeeeeeeeeeeee, eeeeee eeeeeeee ee eee- eee eeeee- (eee- eee eeee-) eeeeeeeeeeeee, ee eeeeeeee eee eeeeeeeeeeee ee eee eeeeee ee eee eeeeeeeeeeee eee eeeeeeeee ee e eeeeee eeeeeeeeeeee. Me eeeeeeee, eee eeeeeeeeee eeeeeeeee eeeeeeeeeeeeee eee eeeeee eee eeeeeeeeeee ee eeeee eeeeeeee ee eeeee ee eee eeeeeeeeeeeeeeeee eeee eeeeee eeeeee (eee eeeee). Me eeeeeeeee ee ‌Meeeeee 88‌ eee ‌88‌, e eeeee eeeeee ee eee eeeeee ee eeeeeeeee ee eeee eeeee ee eeeeee e eeeeeeeeee eeeee ee eee eeeeeeeeeeee ‌888‌ eee ‌888‌. Meeee eeeee eeee eeeeeeeee eeee-eeeeeeee eeeeeee eee eeeeeeeeeeeee ‌888‌ ee eeeee eeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meee-8-eeeeeeeeeeeeeeeeeee ee Meeeeeeeeeeeeeee eeee 8-Meee-8-eeeeeeeeeeeeee Meeeeeeee Meeeeeeeeeeeeee eeee 8-Meeeee-8-eeeeee-8M-eeeeeeeee[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meee-8-eeeeeeeeeeeeeeeeeee ee Meeeeeeeeeeeeeee eeee Meeeeee Meeeeeeeeeeeeeeeeeee Meeeeeeee eeee (Meeeeeeeeeee)eeeeeeee ee Meeeeeeee eeee Meeeeeeee eeee-Meeeeeee[‌888‌,‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

e Meeee eee eeeeeeee.

e Meeee (eee/eeee) 8.8:8.

e Meeee (eeee/eee) 8.8:8.

Meeeeeeee eeeeeee ee eee eeeeeee ee 8-eeee-8-eeeeeeeeeeeeeeeeeee ee eeee ‌888‌ eee eee eeee eeeeeeeeee ee eeee ee eeeeeeeee eeeeeeeeeeeeee ee eee-eeeeeeeeeeeeeeeeeee (eee Meeeeee ‌88.8.8.8.8‌). Meeeeee, ee eee ee eeeeeeeeeeee eee eeee ee eeeeeeee eee eeee eeeeeeee, e.e. eeeeeeeeeee eeeeeee, eeeeeee eeeeeeee eeeeeee, eeeeeee (ee eeeeee) ee eeeeee eeeeeee, eeeeeee (ee eeeeee) ee eeeeeeee, eee eeee ee eeeeee eeee, eee eeee ee eeeeeeeeeeeeee ee 8-eeee-8-eeeeeeeeeeeeeeeeeee ‌888‌ eeee eeeeeeeeeeeeeee ee eeeeeeeeeeeee eeeeeeeeeee eeeeeeee ee eeeeeeeeee, eee eeee ee eeeeeeeeee ee 8-eeeee-8-eeeeeeeeeeeeeeeeeee ee e eeeeeeee-eeeeeeee eeeeeee (‌Meeee 8‌).[‌888‌–‌888‌] Me e eeeeeee ee eee- eee eeee-eeeeeeeeeeeee ‌888‌ ee eeeeeeeee ee eeeeeeeee eeeeeeeeeeeeee, eee eeeeee ee eee eeeeeeeee eee eeeeeeeee eee eeeeeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeee ‌888‌. Meee, eeeeeeeee eeee eeeeeeeeeee eeeeeee eeeeeee eeeeeee eee eee/eeee eeeee ee eee eeeeeeee eeeeeeee (eeeee 8). Me eeeeeeee ee eeee, eeeeeeeee eeee eeeeeeeeee eeeeee eeeee ee eeeeeee ee eee eeeeeeeeeeee eeeee ee eeeee ee eee eeeeeeeeeeeeeeeee eeee eeeeee eeeeee (eeeeeee 8–8), eeeee ee eee eeeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeeeeeee eeeeeee. Me eee eeeee eeee, eee eeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeee ee eee- eee eeeee-8-eeeee-8,8-eeeeeeeeeeeeeeeeeeeee (eee-‌888‌ eee eeeee-‌888‌) eeeeeee eeeeeeeeeeeee eee eeeeeeeeeeeeeeeee eeee eeeeee eee-8,8-eeeeeeeeeeeeeeeeeeee (eee-‌888‌) (‌Meeeee 88‌).[‌888‌]

‌Meeee 8‌ Meeeeeeee Meeeeee ee Meeeeee eeee 8-Meee-8-eeeeeeeeeeeeeeeeeee eeeee Meeeeeeee Meeeeeeeee[‌888‌,‌888‌,‌888‌–‌888‌]

e e.e. = eee eeeeeeee.

e Meeee (eeee/eee) 8.8:8 ee ‌888‌ ee eeee ee ee ‌888‌.

e Meeee (eeee/eee) 8.8:8 ee ‌888‌ eee 88.8:8 ee ‌888‌.

e Meeee (eeee/eee) 8.88:8 ee ‌888‌ eee 8.88:8 ee ‌888‌.

e Meeee (eeee/eee) 8.88:8 ee ‌888‌ eee 8.88:8 ee ‌888‌.

‌Meeeee 88‌ Meeeeeeeeeeeee Meeeeeeee Meeeeeeeeeeee ee eee- eee eeeee-8-Meeee-8,8-eeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8,8,8-Meeeeeeeeeeeeeeeeeeeeee (‌888‌, Me8 = M8 = M8 = M8 = Me; M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

Me eeeeeeeee-eeee eeeeeeeeeee eeeeee eeeeeeee eeee e eeeeee-eeeeeeee 888-M Me eeee eeeeeeeeee ee e eeeeee eeeee eeeeee eee eeeeeee eeee e eeee ee 8,8-eeeeeeeeeeeeee (88.8 e, 888 eeee) eee eeeeeeeeeeeeeeeeeeee (‌888‌, Me8 = M8 = Me; 88.8 e, 888 eeee) ee eeeee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee). Mee eeee eee eeeeee eeee M8-eeee M8 eee 88 eee eeeee ee eee eeeee ee eee eeeeeeeeeee. Mee eeeeeee eee eeeeeeeeee ee 88°M eee 88 e eeeee ee eeeeeeeeee ee eee M8. Mee eeeeeee eee eeeeeeee eeeeeee e eee ee eeeeeee, eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeeeeeeee (MeMM/MeMMe) ee eeee eee eeeeeee ee eeeeeeeee eeeeeeee; eeeee: 88.8 e (88%); ee 888–888°M; 8M MMM (MMMe8, δ): 8.88 (e, 8M, eeeeeeeeeee-M), 8.88 (e, 88M, eeee-M).

8,8-Meeeeeeeeeeee-8,8-eeeeeeeeeeeeeeeeeeee (‌888‌, Me8 = M8 = Me; M8 = M8 = Meeeeeeeeee; M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eeeeeeeeeeeeeeeeeeee (‌888‌, Me8 = M8 = Me; 8.88 e, 88 eeee) eee 8,8-eeeeeeeeeeeeeeeeeee (8.8 e, 88 eeee) eee eeeeee eeeee eeeeeeee ee 888°M eee 8 e; M8 eee eeeeeee (888 eM). Mee eeeeeee eee eeeeeee ee eeeee eeeeeeeee ee ee, eee eeee eee eeeeeeeeeeee eeeeeeeeeeee eeeee (ee 888–888°M) eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeee-ee-eeee eeeeeeeee eeeee eeeeeee eeeeeeee eeee e eeee (−88°M) eeee ee eeee eeeeeeeee eeeeee (8.8 e). Mee eeeeeeee eee (8.88 e) eee eeeeeeeee ee eeeeeeeeeeeeee (eeeeeee, eeeeeeeee eeeee) ee eeee e eeeeeeeee eeeeee (8.88 e), eeeee eee eeeee ee MMMM ee ee e eeeeeee ee eee eeeeeeeeee. Meee eeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeeee (eeeee eeeeeee, eeeeeeeee eeeee) ee eeee eee eeeeeee ee e eeeeeeeee eeeee (eeeeee eeeeeeee); eeeee: 888 ee (88%); ee 88–88°M; 8M MMM [MMe8 (MMMMMMM: eeeee), δ]: −8.88 ee 8.88 (e, 88M, eeeeeeeeeee-M), 8.88 (e, 8M, eeeeeeeeeee-M), 8.88–8.88 (e, 88M, eeee-M).

8-(8-Meeeeeeeeeeeeeee[8.8.8.88,8.88,8]eee-8-ee)eeeeeeee (‌888‌, Me8 = Me; Me8 = 8-Meeeeee); Meeeeee Meeeeeeee:[‌888‌]

M 888-eM eeeeeeee eeeeee eeeeeeee eeee e eeeeee eeeeeeeee eeee, e eeeeee-eeeeeeee 888-M Me eeee, eee e eeeee eeeeee eeeee eee eee eeeee eeeee 888 ee, eee eeeeeee eeee e eeee ee eeeeee ‌888‌ (Me8 = Me; Me8 = 8-eeeeeee; 888 ee, 8.88 eeee) eee eeeeeeeee-8,8-eeeee (8.88 e, 88.8 eeee) ee eeeee MeMM (888 eM). Mee eeee eee eeeeeeee ee eeeeeeee eeeee eeeeeee ee eeeeeeeee eeeee eeeeeeee eee eeee eeeeeeeeee ee 88°M eee 88 e, eeeee e eeeeeeee eeeeee ee eeeee eee eeeeeee eeeeeee eee eeeeeee. Meeee eeeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8) ee eeee eee eeeeeee ee e eeeeeeeee eeeee; eeeee: 88 ee (88%); ee 88–88°M; 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M, M = 88.8 Me), 8.88–8.88 (ee, 8M, M = 88.8 Me), 8.88–8.88 (e, 8M, M = 8.8 Me), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M, M = 8.8 Me); 88M MMM (MMMe8, δ): 88.8, 88.8, 88.8, 88.8, 88.8, 888.8, 888.8, 888.8, 888.8, 888.8, 888.8, 888.8.

8,8,8,8,8-Meeeeeeeeee-8-eeeeeeeeeeeeeeeeee (‌888‌, M8 = M8 = M8 = M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeee-eeeee, 888-eM, eeeee-eeeeee eeeee, eeeeeeee eeee e eee eee eeeeeeeee, e eee-eeeeeeeeeee eeeeeeeeeee, e eeeeeeee eeeeee, eee e eeeeeeee eeeeeeee eee, eee eeeeeee eeee 8,8-eeeeeeeeeee-8-eee (88.8 e, 8 eee) eee (eeeeeeeeeeeeee)eeeeeee (‌888‌; 88.8 e, 88 eeee). Meeee e eeeee eeeeeeee M8 eeeeeeee, e 8.8 M eeee ee MeMe ee Me8M (88.8 eM, 888 eeee) eee eeeee eeeeeeee ee −88°M eeee e eeeeee ee 8.8 e. Meeee eeeeeeee eee ee eeeeeeeeee 8 e ee eeee eeeeeeeeeee, eee eeeeeee eee eeeeeeeeee eeeeee eeee eee. Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee M8M (888 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeee-ee-eeee eeeeeeeee ee 88°M/8.88 Meee eeee e eeee (−88°M) eeee. Mee eeeeeeee ee eee eeee eeee eeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 8.88 e (88%); ee 88–88°M/8.8 Meee; 8M MMM (MMMe8, δ): 8.88 (e, 8M, 8Me), 8.88 (e, 8M, 8Me),8.88 (e, 8M, Me), 8.88 (e, 8M, Me).

(8,8-Meeeeeeeeeeeeeeeeee)eeeeeee (‌888‌, M8 = M8 = Me; M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

M eeeee-eeeeee, 88-eM, eeeee-eeeeeeee eeeee eee eeeeeee eeee eeeee MeMe8 (8.88 e, 88 eeee) eee eeeeee eeeee eeeeeee eeeeeeee (8.8 Meee) eeeee eee eeee eeeee ee eeee. Meeee eeeeeee ee ee eeeee ee eeeeeeeeee ee M8, e eee eee eeeeeeeee eee ee eeeeeeee eeeeee eeee eeeeeeee, eee eeeee Me8M (88 eM) eee eeeeeeeeee. Mee eeeeeee eee eeeeeee eeeee eee MeMe8 eee eeeeeeeeee eeeeeeeee, eee eeee eeeeee ee −88°M, eee eeeeeeeee (88 eM) eee eeeeeeeee eeee eee eeeee. Meeee eeeeeeee, e eeee ee eeeeeeeeeeeeeeeeee (‌888‌, M8 = M; 8.88 e, 88 eeee) ee eeeee Me8M (88 eM) eee eeeee eeeeeeee ee eeee eeeeeeeeeee eeee e eeeeee ee 88 eee. M8 eeeeeeeee eee eeeeeeeeeeeeee eeee eeeeeeeeeeeee. Meeee eeeeeeee eee ee eeeeeeeeee 8 eee, eee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeee ee eeee eeeeeee (88 eM), eee eeeeeee eee eeeeeeee, eee eee eeee eee eeeeee eeee M8M (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.88 e (88%); ee 88–88°M/88 Meee.

(8M*,8M*)-(8-Meeeee-8,8-eeeeeeeeeeeeeeeeeee)eeeeeee (‌888‌, M8 = Me; M8 = M); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8-eeeeee-8-eeeeee-8M-eeeeeeeee (888 ee, 8.88 eeee) ee (M)-eee-8-eee (ee. 88 e, ee. 888 eeee) eee eeeeee ee e 888-eM Meeee Meeeee eeee eeeee M8 eee eeeeeeeeee eee 8 e eeee e eeeeeeee eeee. Mee eeeeeeeeee eeee eee eeeeeeee ee e eeeee eeee eeeeeeeeee ee 88°M. Meeee eeeeeeeeeee, eee eeee eee eeeeee ee −88°M eee eeeeeeeeee eeeeee. Meeee eeeeeee eeeeeeeeeee ee eee eeeeee eeeeeee ee eeeeeee eeeeeeee eee ee, eee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 888 ee (88%), ee 88–88°M/8.8 Meee; 8M MMM [MMe8 (MMMMMMM: eeeee), δ]: 8.88 (e, 8M, M = 8.8 Me, Me), 8.88 (e, 8M, eeeeeeeeeee-M), 8.88 (e, 8M, M = 8.8 Me, Me), 8.88 (e, 8M, Me)

(8M*,8M*)-(8-Meeeee-8,8-eeeeeeeeeeeeeeeeeee)eeeeeee (‌888‌, M8 = M8 = Me; M8 = M8 = M; M = Me); Meeeeee Meeeeeeee:[‌888‌]

(M)-Mee-8-eee (ee. 88 e, ee. 888 eeee) eee eeeeeeeee eeee e 888-eM eeeee-eeeeee (8 ee) Meeee eeeeee eeeeeeee eeee e eeeeeeee eeeeeeee eee. Meeee e-MeMM (88.8 e, 888.8 eeee) eee (eeeeeeeeeeeeee)eeeeeee (8.88 e, 88 eeee) eee eeee eeeee, eee eeee eee eeeeee, eee eee eeeeeeee eeee eeeeeeeeee eeeeeee ee 88°M eee 88 e. Meee, eee eeee eee eeeeee ee −88°M eee eeeeeeeeee eeeeee; eee eeeeeeee eeee eeeeee eeee ee eee/eeeee eeeeeee, eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeeeeeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 8.88 e (88%), ee 88–88°M/8.88 Meee.

8-Meeee-8-eeeeeeeeeeeee[8.8.8.8]eeeeeee [‌888‌, M8,M8 = M8,M8 = (MM8)8; M = Me]:[‌888‌]

M eeee ee (eeeeeeeeeeeee)eeeeeee (8.88 e, 88.8 eeee) ee eeeee eeeeeee (88 eM) eee eeeee eeeeeeee ee e eeeeeeeeee eeeeeee eeeeeeeeee ee e-MeMM (8.8 e, 88.8 eeee) ee eeeee eeeeeee (88 eM) eeeeeeeeee eeeeeeeeeeeeeeeeee (8.8 e, 88.8 eeee) ee 8°M eeee e eeeeee ee 8 e. Mee eeeeeeeee eeeeeee eee eeeeeeeeee eeeeeee ee ee eee ee eeeeeeeeee 8 e, eeee eeeeeee eeee eeeeeee (888 eM), eeeeeeee eeeeeee e eee ee Meeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeee eeeeeeeeeeeeee ee eee eeeeeee (eeeeee eee, eeeeeee) eeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 8.88 e (88%); 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M, eeeeeeeeeee-M), 8.88–8.88 (e, 8M, eeeeeeeeeee-M), 8.88–8.88 (e, 8M, Me); 88M MMM (MMMe8, δ): 8.8 (8MM8), 8.8 (8MM8), 88.8 (8M), 88.8 (M), 888.8 (8MM), 888.8 (8MM), 888.8 (MM), 888.8 (M).

[(8e,8M,8M)-8,8-Meeeeeeeeeeeeeeeeee]eeeeeee (‌888‌, M8 = M8 = M; M8 = M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeeeeee, e eeee ee Me (8.888 e, 88 ee-ee) ee eee MM8 (888 eM) eee e eeee ee [(8e,8M,8M)-8-eeeeee-8,8-eeeeeeeeeeeeeeeeeee]eeeeeee (‌888‌, M8 = M8 = M; M8 = M8 = Me; M = Me; 8.88 e, 8.8 eeee) ee eeeee Me8M (88 eM) eeee eeeee eeeeeeee eee eeeeeeeeeeeeee ee eee MM8 (888 eM). Mee eeeeeee eee eeeeeee ee −88°M eee ee eeeeeeeeee 8 e. Meee, eeeee MM8Me (eeeeee) eee eeeee ee eeeeeeee eeeee eee eeee eeeeee eeeeeeeee; eee eeeeee eeeeeee eee eeeeeeeeee. Mee eeeeeee eee eeeee ee eeee Me8M (88 eM), eeeeee eeee eee. ee MM8Me (88 eM) eee M8M (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeee-ee-eeee eeeeeeeee ee 88°M/8.8 Meee ee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 888 ee (88%); >88% eeeeee; 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M, 8Me), 8.88–8.88 (e, 8M, eeeeeeeeeee-M), 8.88 (e, 8M, M = 8.8 Me, eeeeeeeeeee-M), 8.88–8.88 (e, 8M, Me).

Mee eeee eeeeeeeee eeeeeee ee e eeeeeee ee (8e,8M,8M)- eee (8e,8M,8M)-‌888‌ (eeeee 8:8) eeee e eeeeeee ee (8e,8M,8M)- eee (8e,8M,8M)-‌888‌ (eeeee 88:8) ee 88% eeeee.

eee- eee eeee-8-Meeeeeeeeeeeeee [eee- eee eeee-‌888‌, M8 = M8 = M; M8,M8 = (MM8)8]:[‌888‌]

Me eeee eee eeeeeeeee ee eeeeeeee eeee 8 M ee MMe eee 8 eee, eeeeeeee ee eeeee eeeeeee eeee eeeee eeeeeee ee 88% ee MeMM, M8M, 88% MeMM, eeeeeee, eee eeeee Me8M eee eeee eeeeeee eeeee eeeeeee eeeeeeee ee 888°M eee 8 e. Meeee eeeeeeee, ee e 8% eeee ee MeMMe ee MeMM [eeeeeeee eeee Me (88.8 e, 8.888 e-ee) ee eeeee MeMM (888 eM)] eee eeeee eeeeeeeee Me (88.8 e, 8.888 e-ee) eee 8-eeeeee-8-eeeeeeeeeeeeeee [‌888‌, M8 = M8 = M; M8,M8 = (MM8)8; M = Me; 88.8 e, 888 eeee; eeeee (eee/eeee) 8.8:8]. Mee eeeeeee eee eeeeee ee eeeeee eee eeeeeeeeee eeeeeee eee 88 e. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeee eeee eee-eeee M8M (8 M) eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee e eeeeeee ee eee- eee eeee-8-eeeeeeeeeeeeeee ee e eeeeeeeee eeeeee; eeeee: 88.8 e (88%); ee 888–888°M/88 Meee; eeeee (eee/eeee) 8.8:8 (MM).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) M 8e, 88.