Science of Synthesis

Santi, C., Science of Synthesis Knowledge Updates, (2013) 2, 395.

The reduction of alkyl selenocyanates can be efficiently effected using reducing hydrides such as sodium borohydride[‌11‌,‌12‌] or lithium aluminum hydride,[‌13‌–‌15‌] and the corresponding selenols are obtained by protonation of the corresponding sodium or lithium salts, respectively, under mild acidic conditions. Using this procedure, the synthesis of a variety of selenols (e.g., ‌4‌, ‌6‌, ‌15‌, and ‌16‌) can be achieved starting from the corresponding selenocyanates (‌Scheme 6‌). Using lithium aluminum hydride, α,β-unsaturated selenocyanates (e.g., ‌17‌) afford the corresponding alkaneselenols (e.g., ‌18‌) as a result of the simultaneous reduction of the selenocyanate and the CC bond. However, when remote double or triple bonds are present, chemoselective reduction of the selenocyanate is observed.

‌Meeeee 8‌ Meeeeeeee ee Meeeeeeeeeeeee[‌88‌–‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeee-8-eeeeeee (‌88‌):[‌88‌]

Me e eeee ee eeeee eeeeeeeeeeeee (888 ee, 8 eeee) ee MeMM (8 eM), MeMM8 (888 ee, 8 eeee) eee eeeee ee eeeee eeeeeeee eee eee eeeeeee eee eeeeeee ee ee eee 8.8 e. Meee, 88% ee MMe eee eeeee, eee eee eeeeeee eeeeeeeeee eeee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eeeeee eeee eeeeee eeee M8M (8 × 8 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eeeeee e eeeeeee, eeeee eee eeeeeeeee (88 °M/88 Meee) ee eeee eeeeee-8-eeeeeee (‌88‌); eeeee: 888 ee (88%).

Meeeeeeeeeeeeeeeeee (‌88‌):[‌88‌]

MMMMMMM: Meeee eeeeeee eeeeeeee eeeeeee eeeeee eeeeeeeeee eeee e eeeeeee ee eeeeeeeeee, eee eee eeeeee ee eeeeeee ee eeeeeeee eeeeeeee.

MeMeM8 (8.8 e, 8.8 eeee) eee eeeee eeee eeeee eeeeeeeeee (88 eM) eee eeeeeeeeee eeee e 88-eM eee-eeeeee eeeee eeeeeeee eeee e M8 eeeee. Mee eeeeeee eee eeeeeee ee −88 °M eee 8 eee. Meeeeeeeeee eeeeeeeeeeeee (888 ee, 8.8 eeee) eeeeeeeee ee eeeeeeeeee (88 eM) eee eeeeeeeeeeee eeeee eeeeeeee eee eee eeeeeeeee eeee eee eeeeeee ee −88 °M eee 8 eee. Me e 888-eM eee-eeeeee eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeee, e eeeeeeeeee ee eeeeeeee eeee (8.88 e, 88.8 eeee) ee eeeeeeeeee (88 eM) eee eeeeeeee, eee eee eeeee eee eeeeeeee ee e eeeeee eeee eeeeeeee eeee eee eeeee, eeeeeeee, eee eeeeee ee −88 °M. Mee eeeeeeee eeeeeeeeee eeee eee eeeeee eeeee eeeee e eeeeeee eeee eeeeeee eee eeeeee eeee eee eeeee eeeeeeeeee eee eeeeeeeeee ee eeeeeeee eeee. Meeeee eee eeeee eee eeeeeeee, eeeeeee ‌88‌ eee eeeeeeeee eeeee eeeeee (88−8 eeee). Mee eeeee eeee, eeeee eee eeeeee ee −88 °M, eeeeeee eee eeee eeeeeeee eeeeeeeeee eee eee eeeeee eeee, eeeeeeee eeee eee eeeeeeeee eee eeeeee ee −888 °M, eeeeeeeee eeeeeeee ‌88‌. Me eeeee ee eeeeeee eee MMM eeeeeeee, eee eeeeee eeee eee eeeeeee ee eeee ee ee eee eee eeeeeee eee eeeeeeeee ee e eeee eeeeee (−888 °M) eeeeeeeee ee ee MMM eeee eeeeee ee eee M8. Meeee eeeeeeeeeeeee eeee eee eeeeee, eee eeeeeeeee eee eeeeee eeee M8, eee eeeeeee eee eeeeeeeee ee eee MMM eeee, eee MMMe8 eee eeeee ee eeeeeee. Mee eeeeeee eee eeeeee ee eeeeeeeeeeee eeeee eeee −88 °M; eeeee: 88%.

Meeeeeeeeeeeee (‌8‌):[‌88‌]

Mee eeeeeeeee eee eeeeeeeee eeee eee eee eeeeeeeee ee MeMeM (‌8‌) ee eeeeeeeee ee MeMeMM eee eeeeeeeee ee eeee eeeeeeeee eeeee eee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeee (‌88‌). Meeeee eee eeeee eee eeeeeeee, eeeeeee ‌8‌ eee eeeeeeeee eeeee eeeeee (88−8 eeee). Mee eeeee eeee, eeeeee ee −88 °M, eeeeeee eee eeee eeeeeeee eeeeeeeeee eee eee eeeeee eeee, eeeeeeee eeee eee eeeeeeeee eee eeeeee ee −888 °M, eeeeeeeee eeeeeeee ‌8‌; eeeee: 88%.

Mee-8-eee-8-eeeeeee (‌8‌):[‌88‌]

Mee eeeeeeeee eee eeeeeeeee eeee eee eee eeeeeeeee ee eee-8-eee-8-eeeeeee (‌8‌) ee eeeeeeeee ee eee-8-eeee eeeeeeeeeeeee eee eeeeeeeee ee eeee eeeeeeeee eeeee eee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeee (‌88‌). Meeeee eee eeeee eee eeeeeeee, eeeeeee ‌8‌ eee eeeeeeeee eeeee eeeeee (88−8 eeee). Mee eeeee eeee, eeeeee ee −88 °M, eeeeeee eee eeee eeeeeeee eeeeeeeeee eee eee eeeeee eeee, eeeeeeee eeee eee eeeeeeeee eee eeeeee ee −88 °M, eeeeeeeee eeeeeeee ‌8‌; eeeee: 88%.

References