Science of Synthesis

Murahashi, S.-I., Science of Synthesis, (2004) 19, 360.

Organozinc halides are readily prepared by the insertion of zinc dust into organic halides[‌96‌] or by low-temperature transmetalation of organolithium with zinc salts.[‌97‌,‌98‌] They display an excellent functional-group tolerance allowing the convenient preparation of polyfunctional organozinc compounds. Their moderate reactivity toward carbon electrophiles necessitates transmetalation to the more reactive organocopper or use of a transition-metal (e.g., palladium-based) catalyst.[‌99‌,‌100‌] However, the commercially available tosyl cyanide[‌101‌] reacts readily with various organozinc compounds affording polyfunctional nitriles in good yields.[‌102‌]

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‌Meeeee 88‌ Meeeeeee ee Meeeeeeeee Meeeeeeee Meeeeee Meeee Meeeee eeee Meeeeeeeeeeee[‌888‌,‌888‌]

Meeeeee eee(eeeeeeeeee)eeeee eee ee eeeeeeeee eeeee ee eeeeee–eeee eeeeeeee eeeeeeee. Meee eee eeeeeeeee ee ee eeeeeeeeeeeeeeeee eeee ee eeeeee (8–8 eeeee) ee eeeeeeeeeee ee 88–88°M eeeeeee eeeeeee eeeee ee eeeee eeeeeeee eeee eee eeeeeeeee ee ee eeeeeeeeeeee eeeee eeeeeeeeeee. Mee eeeeee eeeeeeeeeee eee eeeeeeeeee eee eeeeee eee. Meeeeeee ee eeeeee(M) eeeeeee–eee(eeeeeee eeeeeeee) eeeeeee eeeee ee eeeeeeeeeeee eeeeeee eeeee ee eeeeee eeeeeeee eeeeee eeeeeeeeeeeeeee eeee ee α,β-eeeeeeeeeee eeeeeee eee eeeeee, eee eeeeeee eee eeeeeeeee ee 8-(8-eeeeeeeeeeeee)eeeeeeeeeeeee (‌88‌) (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeee ee ee Meeeeeeeee Meeeeee Meeee Meeeee ee α,β-Meeeeeeeeee Meeeeee eee Meeeeeeee Meeeee[‌888‌]

Meeeeeeeeeeeee eeeeeeeeeeee eee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeee eeeee eeeeeee eeee eeeeeeeeeee ee eeeeeeeee eeeeee. Meeee eeeeeeeee eeee eeeeeeeee ee eee eeeeeeee ee eeeeee(M) eeeeeee–eee(eeeeeee eeeeeeee) eeeeeeee eeeeeee eeeeeeee eeeeeeee ee eeee eeeeee. Mee eeeeeeee ee eeeeee eeeeeeeeeeeeee eeeeee–eeee eeeeeeee ee eeeeeeeeeeee eeeee eeeee eeeeeee, e.e. ‌88‌ (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeee ee Meeeee–Meee Meeeeeee ee Meeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-(8-Meeeeeeeeeeee)eeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M Meeeeee eeee eee eeeeeee eeee 8-eeeeeeeeeeeeeeeee (8.88 e, 8 eeee) eee Me8Me (8.8 eM, 88 eeee). Mee eeeeeee eee eeeeee ee 88–88°M eee eeeeeee eee 88 e ee eeee eeeeeeeeeee. Mee MeM eeeeee eee eeeeee Me8Me eeee eeeeeee eeeee eeeeee (88°M/8.8 Meee, 8 e). Mee eeeeeeeee eee, eee(8-eeeeeeeeeee)eeee, eee eeeeeeeee ee eee MMM (8 eM) eee eeeee ee e MMM eeee (8 eM) ee MeMM (888 ee, 8 eeee) eee MeMe (888 ee, 8 eeee, eeeee ee 888°M/8.8 Meee, 8 e) ee −88°M. Mee eeeeeeeee eeeee eeeee eeee eee eeeeee ee −88°M, eee MMMMe (8.8 e, 8 eeee) eee eeeeeeee-8-eeeee (8.888 e, 8.8 eeee) eeee eeeee eeeeeeeeeeee. Mee eeeeeee eee eeeeee eeeeeee ee eeee ee −88°M eeeeeeeee eee eee eeeeee ee ee eee eeeee eee. Meeeeeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8) eeee eee eeeeeee; eeeee: 888 ee (88%).

8-Meeeeeeeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeeeee-8-eee (8.88 e, 8.8 eeee) eee eeeee ee −88°M ee e MMM eeee ee eee (8-eeeeeeeeeee)eeeeee eeeeeeeeee (88 eeee). Meeee eeeee eeeeeeeeee, e eeeeeee ee eeeeee eee eeeee eee eeeeeeee. Mee eeeeeee eee eeeeeee eeeeeee eeeeeeeee ee e 88% MMe eeee (88 eM) eee eeeeee ee. Mee eeeeeee eeeeee eee eeeeeeee ee eee eeeeeeeee eeeeeee eeeee eeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8 ee 8:8); eeeee: 8.88 e (88%).

References

Meeeeee Meeeeeeeeee

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