A General Synthetic Method for the Preparation of Conjugated Dienes from Olefins Using Bromomethanesulfonyl Bromide: 1,2‐Dimethylenecyclohexane

Abstract

A general synthetic method for the preparation of conjugated dienes from olefins using bromomethanesulfonyl bromide: 1,2‐dimethylenecyclohexane intermediate: bromomethanesulfonyl bromide intermediate: 1‐bromo‐1‐methyl‐2‐(bromomethylsulfonyl)cyclohexane (54.0 g, 0.16 mol) in tert‐butyl alcohol–tetrahydrofuran (9 : 1, 100 mL) product: 1,2‐dimethylenecyclohexane product: C 3 H 7 CHCHCHCH 2 product: C 5 H 11 CHCHCHCH 2 product: (E)‐C 3 H 7 CHCHC(C 4 H 9 )CH 2 product: (E)‐C 4 H 9 CHCHC(CH 3 )CH 2 product: (E)‐C 4 H 9 CHCHC(CH 3 )CH 2 + CH 2 CHC(C 5 H 11 )CH 2 product: PhCHCHCHCH 2 product: PhOCHCHCHCH 2 product: HO(CH 2 )8CHCHCHCH 2 product: (CH3)3SiCHCHCHCH 2 product: CH 2 CH(CH 2 )5CHCHCHCH 2 product: CH 2 CHCHCH(CH 2 )4CHCHCHCH 2 product: (CH 3 )2Si(CHCHCHCH 2 )2