STEREOCHEMICAL DEPENDENCE OF THE BIS-ALKYLATION REACTION OF ALPHA,ALPHA-DILITHIATED ALLYL PHENYL SULFONE WITH CIS- AND TRANS-1,4-DICHLORO-2-BUTENE - A CONVENIENT METHOD FOR THE SYNTHESIS OF A CYCLOHEPTA-1,4-DIENE SYSTEM
Ta. Houston et M. Koreeda, STEREOCHEMICAL DEPENDENCE OF THE BIS-ALKYLATION REACTION OF ALPHA,ALPHA-DILITHIATED ALLYL PHENYL SULFONE WITH CIS- AND TRANS-1,4-DICHLORO-2-BUTENE - A CONVENIENT METHOD FOR THE SYNTHESIS OF A CYCLOHEPTA-1,4-DIENE SYSTEM, Synthetic communications, 24(3), 1994, pp. 393-398
While the bis-alkylation of the dilithio derivative of allyl phenyl su
lfone with cis-1,4-dichloro-2-butene produces the cyclopentene product
, the similar reaction with the trans-dihalide affords the divinylcycl
opropane product which rearranges smoothly, upon refluxing in xylenes,
into the 1,4-cycloheptadiene system in 65% overall yield from allyl p
henyl sulfone.