Synthesis of substituted cyclic 1, 3-dienes via selective 1, 4-elimination of benzenesulfinic acid from allylic phenyl sulfones

M Sellen, JE Baeckvall, P Helquist

Index: Sellen, Mikael; Baeckvall, Jan-E.; Helquist, Paul Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 835 - 839

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Citation Number: 32

Abstract

29 30 possibilities for 1, 4elimination of benzenesulfinic acid from 29, one would give a 1, 3- cyclohexadiene, the other a methylenecyclohexene. It turned out that the exocyclic elimination was highly favored from 29, using the same reaction conditions as above, and 30 was the only product formed (> 96% exocyclic diene). I2 This selectivity reflects the higher kinetic acidity of the allylic CHB compared to the other allylic proton.