The cleavage of two carbon-carbon bonds in a Wolff-Kishner reduction

✍ Scribed by Robert P. Lemieux; Peter Beak

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 188 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99463-2

✦ Synopsis

The reaction of dispiro[cyclopropane-l,l'-indan-3',1"-cyclopropane]-2'-one

(1) under Wolff-Kishner conditions gives spiro[cyclopropane-l,l'-indan]

(2) in which the ketone has been reduced and two bonds of one cyclopropane ring have been cleaved.

The Wolff-Kishner reaction is a classic method for the complete reduction of aldehyde and ketone carbonyl functions to methyl and methylene groups. 1 Although cases in which a Wolff-Kishner reduction is accompanied by loss or migration of heteroatoms or double bonds a to the carbonyl group are well documented,1 only a few instances in which a single (x carbon-carbon bond is cleaved during the reaction have been reported.laP2 In this