E. Block, M. Aslam
Apr 28, 2003
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Journal
Organic Syntheses
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: C3H7CHCHCHCH2 product: C5H11CHCHCHCH2 product: (E)-C3H7CHCHC(C4H9)CH2 product: (E)-C4H9CHCHC(CH3)CH2 product: (E)-C4H9CHCHC(CH3)CH2 + CH2CHC(C5H11)CH2 product: PhCHCHCHCH2 product: PhOCHCHCHCH2 product: HO(CH2)8CHCHCHCH2 product: (CH3)3SiCHCHCHCH2 product: CH2CH(CH2)5CHCHCHCH2 product: CH2CHCHCH(CH2)4CHCHCHCH2 product: (CH3)2Si(CHCHCHCH2)2 Keywords: addition, to CC; elimination, dehydrohalogenation; halogenation, bromination; oxidation, miscellaneous; photochemical reactions; rearrangements; tert-butyl alcohol; tetrahydrofuran; circulating bath, pump; photochemical apparatus