A simple one-pot preparation of 1-arylsulfonylbicyclobutanes from γ,δ,-epoxysulfones

✍ Scribed by Yehiel Gaoni

• Book ID: 104235250
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 92 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82950-6

✦ Synopsis

Abstracts: Sequential treatment of y,b-epoxysulfones with butyl lithium, methanesulfonyl chloride, and butyl lithium provides 1-arylsulfonylbicyclo[l.l.O]butanes in over 50% overall yields.

We have previously shown that l-(arylsulfonyl)-Z-(hydroxyalkyl)bicyclobutanes could be obtained from y,6-epoxysulfones (1) by dehydration of alcoholsz, epoxidation of the resulhl tant 2-vinylcyclopropane derivatives and base treatment of the epoxide.

1 We report now on a simpler preparation of bicyclobutanes ( 2)) devoid here of the hydroxyl function, by base treatment of the methanesulfonate esters (3) of alcoholsz: Al