Science of Synthesis

Oshima, K., Science of Synthesis, (2002) 4, 725.

Vinylsilanes possessing various functional groups are useful for organic synthesis. (1-Bromoalkenyl)silanes are widely used as key compounds for the preparation of functionalized vinylsilanes. The lithio species generated from dibromobis(trimethylsilyl)methane, bromobis(trimethylsilyl)methyllithium (‌56‌), transforms aldehydes into (1-bromoalkenyl)silanes ‌57‌, no stereoselectivity being observed.[‌31‌] Ketones do not behave as aldehydes, but the analogous (1-bromoalkenyl)silanes ‌59‌ can be obtained by an alternative route[‌31‌] starting from dibromoalkenes, (‌58‌, R1R2C=CBr2). The best route to (1-bromovinyl)trimethylsilane (‌18‌) is starting from trimethyl(vinyl)silane itself; the method can provide the desired compound readily on a large scale (‌Scheme 20‌).[‌32‌,‌33‌]

‌Meeeee 88‌ Meeeeeeeeee ee (8-Meeeeeeeee)eeeeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeeee

(8-Meeeeeeee-8-eeee)eeeeeeeeeeeeeee (‌88‌, M8 = Me):[‌88‌]

Meeee ee (MMM)8MMe8 (88.88 e, 88.8 eeee) ee MMM (88 eM) eee MeMe (88 eeee) ee eeeeeee (88 eM) eeee eeeee eeeeeeeeeeeeee ee −888°M ee eee eeeeeeee eee eeeeeeeeeee eeeeeeeee. Mee eeeeee eeeeee-eeeeee eeee eee eeeeeee eee 88 eee ee −888°M, eee eeee MeMMM (8.8 e, 888 eeee) ee MMM (88 eM) eee eeeee. Mee eeee eeeeee eeeeeeeeee eeeeeeeee eeeeee 8 eee. Meeee e eeeeeee 88 eee ee −888 ee −888°M, eee eeee eee eeeeeee ee eeee ee ee. Me eee eeeeeeeeeee eeee, eee eeee eeeeeeeee eeeeee eee ee eeeee. Mee eeeeeee eee eeeeeeeeeee ee e 888-eM eeeeeeeeee eeeeee eee eee eeeeee eeee ee 8.8 M MMe (8 × 888 eM) ee eeee e eeeeee eeeeeee eeeee, eeeee eee eeeee (MeMM8). Meeeeeeeeeeee ee eee eeeeee eeeeeeeeee eee eeeeeeee ee MMM eeeeeeeeeee (M&M 8888, 8′MMM88, 888°M). Meee eeeee eeeeeeee eeee eeeeeeeeee ee eeeee MMM eeeeeee ee (ee eeeee ee eeeeeee, MM eeeeee): [(8M)-8-eeeeeeeee-8-eeee]eeeeeeeeeeeeeee [(M)-‌88‌] (88%), [(8M)-8-eeeeeeeee-8-eeee]eeeeeeeeeeeeeee [(M)-‌88‌] (88%), eeeeeeee(eeeeeeeeeeeeee)eeeeeee (8%), eee 8-eeeeee-8,8-eee(eeeeeeeeeeeeee)eeeeeee (8%).

(8-Meeeeeeeee)eeeeeeeeeeeeeee (‌88‌):[‌8‌]

Meeeeeeee eeee (Meeeeeeee, Me.; Meee; Meeee; Meeeee, Meeeeee Meeeeeeee), Meeeeeeee (8888), e 8888, eeee eeeeeeeeee eeee Meee Meeee&Meee, Mee.

M 8-M, eeeee-eeeeee, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeeeee eeeeeee eee e 888-eM eeeeeeee eeeeee eee eeeeeee eeee eeeeeeeee(eeeee)eeeeee (88.8 e, 8.88 eee). Mee eeeeeeee ee eee eeeee eeee eeeeeee eee eeeeee ee −88°M, eee Me8 (888 e, 8.88 eee) eee eeeee eeeeeeee eeee ee. 8 e. Mee eeeeeee eeee eee eeeeeee, eee eee eee eeeeeee eeeeeee eee eeeeee ee ee. Mee eeeee eee eeeeee eeee ee eeeeeeeee, eeeee-eeeeee eeeeeeeee, eee Me8MM (888 e, 888 eM, 8.88 eee) eee eeeeeeeeee eeeee eeee eeeeeeeee eeeeeeee. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeee ee eeeeee eee 88 e, eeeeee eeeee eeee e eeeeeeeeeee ee Me8MM8+Me− eeeeee. Mee eeeee eeee eeeeeeeee eeee eee eeeeee eeeeeeeeee ee eeeeeeeeee eee eeeeee eeee eeeeeee 888-eM eeeeeeee ee Me8M. Mee Me8M eeeeeeee eee eeeeeeeee eeeeee, eeeee eeee 888-eM eeeeeeee ee 88% MMe eeeee eee eeeeeee eeeee eeeeeeee eeeeee (eM ee. 8), eeee eeee M8M (888 eM) eee eee. ee MeMe (888 eM). Mee Me8M eeee eee eeeee (MeMM8), eeeeeeeeeeee ee e eeeeee eeeeeeeeee, eee eeeeeeeee eeeeeee e 88.8-ee Meeeeee eeeeee, eeeeeeeee ‌88‌; eeeee: 888–888 e (88–88%); ee 88–88°M/888 Meee.

References

Meeeeee Meeeeeeeeee

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