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

Authors
HOUSTON TA KOREEDA M
Citation
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
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
24
Issue
3
Year of publication
1994
Pages
393 - 398
Database
ISI
SICI code
0039-7911(1994)24:3<393:SDOTBR>2.0.ZU;2-6
Abstract
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.