Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content.
1.1.9.5.2 Hydrocyanation of Alkenes To Form Branched Nitriles

DOI: 10.1055/sos-SD-212-00182

Tauchert, M. E.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20141334.

The earliest example of the hydrocyanation of alkenes to form branched nitriles dates back as early as 1954 and employs octacarbonyldicobalt(0) as the catalyst. However, due to the harsh conditions and a very limited substrate scope, this method is of limited synthetic interest.[‌6‌] Cobalt–salen complex 52 catalyzes the formal hydrocyanation of alkenes under mild conditions, with high selectivity for the branched nitrile (Scheme 24).[‌49‌] Instead of hydrogen cyanide, tosyl cyanide and phenylsilane are used as reagents.

Meeeee 88 Meeeee-Meeeeeeee Meeeeeeeeeeeee eeee Meeee Meeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meee (e) Meeee (%) Mee
Me M M M 8 88 [‌88‌]
Me Me M M 8 88 [‌88‌]
MMMMMM M M M 8.8 88 [‌88‌]
MMMMMM Me M M 8.8 88 [‌88‌]
MM8MM8Me M M M 8.8 88 [‌88‌]
M(M)MMMe Me M M 8 88 [‌88‌]
MM8Me M M M 8 88 [‌88‌]
MMMMMM M Me Me 8 88 [‌88‌]

Mee eeeeeee 88, 88, eee 88, eeeeee eeeeeee eee eeeeeeee eeee eee eeeeee eeeeeeee ee eeeeee ee eeee eeee eeeee eeeeeee eee-88 eee eeee-eeeee eeeeeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeee-Meeeeeeee Meeeeeeeeeeeee eeee Meeee Meeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Meeeeeee 88 (8 ee, 8.888 eeee, 8 eee%) eee eeeeeeeee ee eee MeMM (8 eM) ee ee eeeee eeeee. Meeee 8 eee, eee eeeeee (8.8 eeee) eee eeeee ee eee eee eeee eeeeeeee ee MeMM (88% eeeeee; 888 ee, 8.8 eeee, 8.8 eeeee). Meeeeee, MeMeM8 (88% eeeeee; 88 µM, 8.8 eeee, 8.8 eeeee) eee eeeeeee eeeeeee ee MeMM (8.8 eM) eeee eeeee. Mee eeeeeeeee eeee eee eeeeeee ee ee eee eee eeeeeeee eee eeeeeeeee ee MMM. Meeee eeeeeeeeee ee eee eeeeeeee (8–8 e), eee eeeeeee eee eeeeeee ee eeeeeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee ee eeeeee eee eeeeeeeeeeeee eeeeeee 88.

8-[(8M,8M,8M)-8-Meeeeee-8-eeeeeeeeeeeeeeee]-8-eeeeeeeeeeeeeeeeeeee (88), 8,8,8-Meeeeeeeeeeeeeee[8.8.8]eeeeeee-8-eeeeeeeeeeee (88), eee 8-Meeeee-8-eeeeeeeeeeeeeeeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Meeeeeee eee-88 (8.8 ee, 8.888 eeee, 8 eee%) eee eeeeeeeee ee MeMM (8 eM) ee ee eeeee eeeee. Meeee 8 eee, eee eeeeee 88, 88, ee 88 (8.8 eeee, 8.8 eeeee) eee eeeee, eeeeeeee ee MeMM (888 ee, 8.88 eeee, 8.8 eeeee). M 8.8 M eeee ee e-MeMMM ee eeeeee (88 µM, 8.88 eeee, 8.88 eeeee) eee eeeee ee eee eeeee eeee, eeeeeeee ee MeMeM8 (88 µM, 8.8 eeee, 8.8 eeeee) eee eeeeeee eeeeeee ee MeMM (8 eM). Mee eeeeeeeee eeee eeeeee, eeeeeeeeeee eeee eee eeeeeee ee ee eee eee eeeeeeee eee eeeeeeeee ee MMM. Meeee eeeeeeeeee ee eee eeeeeeee (8 e), eee eeeeeee eee eeeeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee.

References