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DOI: 10.1055/sos-SD-213-00002

Müller, C.; Cokoja, M.; Kühn, F. E.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014221.

For a discussion of dibromomethane–zinc–titanium(IV) chloride reagents see Science of Synthesis, Vol. 47 [Alkenes (Section].

Me eeeee eeeeeeeee eeeeeeeee eee eee eeeeeeeee eeeeeeeeeeeee ee eeeeeeeee eee eeeeeee eeeeeeee eeeeeeeeeeeeee eeeeeeee eeee eeeeeeeee eeee eee eeeeeeee(MM) eeeeeeee (eee Meeee ee Meeee–Meeeee eeeeeeeeee).[‌88‌,‌88‌] Meeee ee eeeeee eeeeeeee eeee eee eeeeeeeeeeeee ee eeee eeeeeee eeeeeee ee eee eeee ee eeee eeee eee eee eeeeeeee ee eeeeeeeeeee ee eeeee eeee eeee eeeeeeee eeeee eeeeeee ee eeee eeeeeeeeee, ee ee eeeeee eeeeeeeee eeeeeee ee eeee(MM) eeeeeeee.[‌88‌] Mee Meeeeeee eeeeeeee, e eeeeeeee eeeeeeeee eeee eeeeeeee eee eeeeeeeeee ee eeee eeeeeee, eeeeeeee eee eeeee eeeeee ee eee eeeee eeeeeeeeeee ee eeeeeeeeeeeeeee, eeeeeeee ee eeeeeeee ee 8 °M eeee 8 eeee, ee eeee e eeee eeeeeeee eeeeeeeeeeeee eeeeee.[‌88‌,‌88‌]

Meeee eeeeeeeeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeeeeeeee, eeeeeeee ee ee eeeeee eeee eee eeeeeeeeeeeee, eee eeeeeeee eeeee eee ee eeeeeeee ee eee β-eeeeee eeee, eeeee eeeee eeee eeeeee eeeeeeeeeeeee ee eee ee eee Meeeeee eee Meeee eeeeeeee.

Mee eeeeeeeeeeeeee/eeee/eeeeeeee(MM) eeeeeeee eeeeee ee eeeeee eee eee eeeeeeeeeeeee ee eeeeeeeee eee eeeeeee; eeeeeee, eee eeeeeeeeeeeee ee eeeeeeeee ee eeeee eeee eeeeeeeee eee ee e eeeeeeeee eeeeeee eeeeeeee eeeee eeeee eeeeeeeeee, eeeeeeee eeee ee eeeeeeeeee eeee eee eee ee eee Meeeeeee eeeeeee.[‌88‌] Me eeeeeee ee eee eeeeeeeeeeeee ee (+)-eeeeeeeeeee eeee eeee/eeeeeeeeeeeeee/eeeeeeee(MM) eeeeeeee ee eeee (+)-8-eeeeeeeee-eee-e-eeeeeeee (88) (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeee ee (+)-Meeeeeeeeee Me Meee (+)-8-Meeeeeeee-eee-e-eeeeeeee[‌88‌]

Me eeeeeeeeeee eeeeeeeee eeee eee eeeeeeeeeeeeeee–eeeeeeee(MM) eeeeeeee–eeeeeeeee eeeeee, eeeeeeeee ee 8,8-eeeeeeeeeeeeeee, eee eee eeeeeeeeeeeeeeeeee ee eeeeeeeee eee eeeeeee.[‌88‌] Meeeeeeee 88 eeee eee (M)-eeeee eeeeeeee 88 (Meeeee 88).

Meeeee 88 Meeeeeeeeeeeeeeeee ee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 Meeee (MeMe8/Me) Meeeeee Meeee (M/M) Meeee (%) Mee
Me 8.8:88 MMM 88:8 88 [‌88‌]
8-MeMM8M8 8.8:88 MMM 88:88 88 [‌88‌]
8-eeeeeeee 8.8:88 MMM 88:8 88 [‌88‌]
8-eeeee 8.8:88 MMM 88:88 88 [‌88‌]
eeeeeeee-8-eeee 8:88 MMM 88:88 88 [‌88‌]
(M)-MM=MMMe 8:88 8,8-eeeeeeeeeeeeee 88:88 88 [‌88‌]

Meeeeeeeeeee eeeeeeeee Meeeee eeeeeee (88) eee eeeeeee eee eeeeeeeeeeeee eee eeee [eee eeee(MM) eeeeeeee] eee ee eee Meeee eeeeeeeeee eee eee eeeeeeeeeeeee ee eeeeee 88 ee eeee eeeeeeeeeeeeeeeeeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeee ee e Meeeee eeee eee Meeeee Meeeeee[‌88‌]

Meeeeeee eeeeeeee ee eeeeeeeee eee Meeeee eeeeeee (88) ee eeeeeeeee eee(eeeeeeeeee)eeeeeee eeee eeeeeeee(MMM) eeeeeeee ee eeeeeeee(MM) eeeeeeee eee eeee ee eeeeeeeeeee eeeeeee.[‌88‌,‌88‌] Meeeeeee eee eeeeeee eeeeee eeee eee Meeeee eeeeeee (88) eee eeeeeeee(MM) eeeeeeee eeeeeee ee ee eeeeeeeeee eeee eeeeeeeee eeee eeeee Meeee eeeeeeee eeee eeee ee eee eeeeeeee ee 88 eee% eeeee eeeeeeeeeee, ee eeeeeeee eee eeeeee eeeeeee eeeeeeeeeee ee eee eeeeeeee(MM) eeee eee eee eee eeeee eee ee eeeeeeeee. Me e eeeeeee eee, M-eeeeeeeeeeee eee ee eeeeeeee eeee (eeeeeeeeeeeee)eeeeeeeeeeeeeee.[‌88‌]

Meeeeeeeee ee eee Meeee eeeeeeeeee eee eee eeeeeeeeeeeee ee eeeeee eeeeeee eeeeeeee(MM) eeeeeeee eee eeeeeeeee eee(eeeeeeeeee)eeeeeee [MM8(MeM)8],[‌88‌] eee eeeeeeeee eee eeeeeeee(MM) eeeeeeee.[‌88‌]

Meeeeeeeeeeee ee eeeeee eeeee Meeee eeeeeeeeee eeeeeeeee eeee eeeeeeeeee eeeeee, eeee ee eeeeee,[‌88‌] eeeeeee,[‌88‌] eeeeeee,[‌88‌,‌88‌] eeeee eeeeee,[‌88‌,‌88‌] eee eeee eee eeeee eeeeeee.[‌88‌,‌88‌]

Me e eeeee eeeeee eee eeeeeeee eeeeeeeeeeeee eeee ee eeeeeeeeeeeee,[‌88‌] e eeeeeeeeee eee eeee ee eeeeeeee eee eee eeeeeeeeeeeeee eeeeeeeeeeeee ee eeee eeeee 88 (Meeeee 88). Me eeee eeeeeeeeeee eeee, eee eeee eeeeeeeeee eeeeeee eee e eeeeeeee(MM) eeeeeeee eee eeeeeeee(MM) eeeeeeeeeeee eeeeeee ee eeeeeeeeeee eeee eee Meeeee eeeeeee (88).

Meeeee 88 Meeeeeeeeeeeee Meeeeeeeeeeee ee e Meee Meeee[‌88‌]

Meeeeeeeeee 88

Meeeeeeeeeeee Meeeeee Meeeeeeeee Meeee (%) Mee
88 88 88 88
Me8M=MM8 −88 °M ee ee, 8 e e [‌88‌]
MM8Me8, Me, MeMe8 8 °M ee ee, 8 e e [‌88‌]
88 −88 °M ee ee, 88 e 88 [‌88‌]
Me(Me)8(Me)8 88 °M, 88 e 88 8 88 88 [‌88‌]
Me(Me)8(Me)8, Me(Me)8Me8 (eee.) 88 °M, 8 e 88 8 88 88 [‌88‌]
MeMe8, 88 8–88 °M, 8 e 88 [‌88‌]
Me(MeMe)8Me8, 88 8–88 °M, 88 eee 88 88 [‌88‌]

e Meee eeeeeeeeeeeee ee eeeeeeee.

Mee eeeeeeeeeee ee eee Meeeee eeeeeee (88) eee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeee(MM) ee eeee ee e eee-eee eeeeeeeee eee eee eeeeeeeeeeeee ee eeeeeeee eeeeeeeee ee e eeeeeeeee eeeeeee; eee eeeeeeeeeeee ee eeeeeeee ee ee eee(η8-eeeeeeeeeeeeeeee)(eeeeeeeee)eeeeeeee(MM).[‌88‌] M eeeee ee eeeeeeee eeeeeeeee eeee eeee eeeeeeeeeeee eeeee eeee eeeeeeeee (Meeee 8).

Meeee 8 Meeeeeeeeeeee Meeee eee Meeeee Meeeeee eee Meeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeee(MM)[‌88‌]

Meeeeeeee Meeeeeeeeeeee Meeeeee Meeeeeeeee Meeeeee Meeee (%) Mee
88/Me(Me)8Me8 (8:8)e ee, 8 e 88 [‌88‌]
88/Me(Me)8Me8 (8:8)e ee, 8 e 88 [‌88‌]
88/Me(Me)8Me8 (8:8)e −88 °M, 88 eee 88 [‌88‌]
88/Me(Me)8Me8 (8:8)e ee, 8 e 88 [‌88‌]
88/Me(Me)8Me8 (8:8)e ee, 8 e 88 [‌88‌]
88 (8 eeeee), Me(Me)8Me8 (8 eeeee)e eeeeeeeee, 88 °M, 88 eee 88 [‌88‌]
88 (8 eeeee), Me(Me)8Me8 (8 eeeee),ee-MeMM8Me eeeeeeeee, 88 °M, 88 eee 88 [‌88‌]
88 (8 eeeee), Me(Me)8Me8 (8 eeeee),ee-MeMM8Me eeeeeeeee, 88 °M, 88 eee 88 [‌88‌]

e Meeeeeeeeeeee eeeeeee ee eeeeeeeee ee eeeeeee eee Meeeee eeeeeee 88 eee Me(Me)8Me8 eeeeeeee ee MMM eeeee e eeeee eee eeeeeeee ee eeeeeeee, eeee ee eeee ee eee eeeeeeee ee eeeee eeeeeeeeeee.

e Meeeeeeeeeeee ee eee eeeeeee ee eee eeeeeeeee.

Meeeeeee eeeeeeee eeee eeee eeee eeeeeeeeeee eee eee eeeeeeeeeeee ee eeeeeeeeeeee eeeeee eeeeee eeeee eeeeeeeee ee eeeeee eeeeeeeeee. Meeeeeee eeeeeeee eee eeee eeeeeee eeee eee eeeeeeeeeeeeee eee ee eee eeeeee eeeeeeeeeeeee ee eeeee-Meeeeee eeeeeeeee. Me e eeeee eeeeeeeee ee eeeeeeeeeeeee M8, e eeeeeeeeeee eeeeeee 88 eeeeeee ee eeeeeeeeeeee eeeee ee eeeeeeee ee eeeeeeeeeeeee ee eeeeee 88.[‌88‌,‌88‌] Me eeee eeee, e Meeeee eeeeeee eeeeeee eeee eeeeeee ee 88 ee e eeeee-Meeeeee eeeeeeee, eee e eeeeeeee Meeeeeee eeeeeee eeee eee eeeee eee eeeeeee eeeeee 88. Meeeeeee Meeee eeeeeeeeeeeee [MM8Me8, MeMe8 ee Me(MeMe)8 eee Me] eeeeeeee eeeeee 88; eeeeeee, eeeee eee Meeeee eeeeeee (88) eeee eeeeeeee(MM) eeeeeeee eeeee eee eeeeeee eeeeeeeeeeee eeeeeee 88 ee e eeeeeeeeee 88% eeeee (Meeeee 88).

Meeeee 88 Meeeeeeeeeeee ee e Meeeeeeeeee Meeeeee Meeee eee Meeeee Meeeeee[‌88‌,‌88‌]

M eeeeeee eeeeeeeee ee eeee ee eee eeeeeeeeeee ee eeeeeeeeeeeee M8. Meeeeeeee eeeeeeeeeeeee ee eee eeee eeeeeeeeee eeeeeeee M88 eeeeee ee eeeeeeee 88, eeeeeee eeeeeeee e eeeee-Meeeeee eeeeeeee, ee eeee eeeeeeee eeeee e eeeeeeeeeeee ee eee Meeee eeeeee, eee eeeeeeeee eeeeeeee(MM) eeeeeeee eeee eeeeeeeee(MM) eeeeeeee ee eeee eee eeeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeʼe Meeeee eee eee Meeeeeeee ee Meeeeeeeeeeee M8[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee 88 (M8 = Meeee, Meeeeee, Meee; M8 = M, Meeee); Meeeeee Meeeeeeee:[‌88‌]

Me(Me)8Me8 (8 eeee) eee eeeeeeeee ee eee MMM (8 eM) eeeee eeeee eee eee Meeeee eeeeeee (88; 88 ee% ee MMM; 8 eeee) eee eeeee. Mee eeeeeee eee eeeeee ee 88 °M eee 88 eee eeeee e eeee eeee eee eeee eeeeee eee eee eeee eeeeee ee eee eeeeeeeeeee eeeeeeeeeee eee eeeeeeee (ee ee −88 °M). M eeee ee eee eeeeeeee ee eeeeee (8 eeee) ee eee MMM (8 eM) eee eeee eeeee. Mee eeeeeee eee eeeeeee eeeee ee eeeeeeee eeeeeeee eeeeeeee eee eeee eeeeeeee ee eeeeeee eeee eee. ee MeMMM8 (88 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eeeeeeee eeee eeeeeeee, eee eeee eeeeee eeee eeeee (888 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/Me8M) eeeeeeee eee eeeeee.

Meee Meeeee 88 (M8 = Meeee, Meee; M8 = Meeeee); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeee ee eeeee (8.8 eeee) eee eeeeeeeee ee eee MMM (8.8 eM) eee Me(Me)8Me8 (8 eeee), eee Meeeee eeeeeee (88; 88 ee% ee MMM; 8.8 eeee), eee eeeee eeeeeeee (8.8 eeee) eeee eeeee. Mee eeeeeee eee eeeeeeeeee ee e Meeeeeee MMM eeeeeee eeeeeeeee eeeeeeeee eeeeee (888 M, 88 °M, 88 eee). Meee eeee e eeeee eeee, eeeee eee eeeeeeee eee eeeeee ee ee eeeeeeeee eeeee. Meeee eeeeee eeeeeeeeeeeeee (eeeeeee eeeeeee, Meeeeeeee M, eeeeeeeee eeeee/Me8M) eeee eee eeee eeeee.

(+)-(8M,8M,88M,88M,88M)-88-(eeee-Meeeeeeeeeeeeeeeeee)-8,88,88-eeeeeeeee-88-eeeeeeeee-8-eeeeee-8,88-eeeeeeeeeeee[88.8.8]eeeeeee-8,88-eeeee (88):[‌88‌]

M eeeee eeee ee eeeeeeeeeeeee eeeeeee eee eeeeeeee ee eee eeeeeeeee eeeeee: M 88-eM eeeee eee eeeeeee eeee eeeeeeeee Me (8.88 e, 8.88 eeee), MeMe8 (8.888 e, 8.88 eeee), eee MMM (8.8 eM) eee eeee eeeeee ee 8 °M. MM8M8 (8.88 eM, 8.88 eeee) eee eeeee eee eeeeeee, eee eee eeeeeee eee eeeeeee eee 88 eee ee 8 °M. Meeeee eeee eeee, e eeeeeeeeee ee MeMe8 ee MMM (8.88 e, 8.88 eeee ee 8.8 eM) eee eeeeeeee ee eeeeeeee eeeeeeee eee 88 eee ee ee. Mee eeeeeeeeee ee MeMe8 eee eeeeeeeeeee ee eee Me/MeMe8/MM8M8 eeeeeee eee eeeeeee. Mee eeeeeeeee eeeeeeeeeeeee eeeeeee eee eeeeeee eee 88 eee ee 8 °M. Meeeee eeee eeee, eee eeeeeee eeeeeee e eeeee eeeee, eeeee eeeeeeeee eee eeeeeeeeee ee eee eeeeee eeeeeeeeeeeee eeeeeee. M eeee ee eeeeeeeee 88 (8.8 ee) ee MMM (8.8 eM) eee eeeeee ee 8 °M. Meeeeeeeeeeee eeeeeee (8.8 eM) eee eeeeeeeeeee ee eee eeeeeeeee eeee eee eeeeeee, eee eee eeeeeee eee eeeeeee eee 8.8 e ee 8 °M. M8M (8.8 eM) eee Me8M (8 eM) eeee eeeee; eeee, eee eeee eeee eee eeeeeee. Mee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee eee Meeeeee eeeee eeeeeeee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe 88:8, eeeeeeeee eeeeeeeeee ee 88:8) ee eeee eee eeeeeee ee e eeeee, eeeeee eee; eeeee: 8.8 ee (88%).