A NEW GENERAL-ROUTE TO 1,2-DIARYLETHYLENES, 1,4-DIARYLBUTADIENES AND 1,6-DIARYLHEXATRIENES THROUGH CYCLOAROMATIZATION OF BETA-OXODITHIOACETALS

A new general route for the title olefins 5a-e, 12, 13, 8a-e and 11 a-e has been developed through nucleophilic addition of respective Grignard reagents i.e. allyl-, benzyl-, 1-(naphthylmethyl) magnesium halides to 5-aryl-1,1-bis(methylthio)pent-4-en-3-ones, 7-aryl-1,1-bis(methylthio)hepta-4,6-dien-...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 11; pp. 1075 - 1077
Main Authors RAO, CS, SINGH, OM, ILA, H, JUNJAPPA, H
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALPHA-OXOKETENE DITHIOACETALS
ANNELATION
OXOKETENDITHIOACETALS
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Summary:A new general route for the title olefins 5a-e, 12, 13, 8a-e and 11 a-e has been developed through nucleophilic addition of respective Grignard reagents i.e. allyl-, benzyl-, 1-(naphthylmethyl) magnesium halides to 5-aryl-1,1-bis(methylthio)pent-4-en-3-ones, 7-aryl-1,1-bis(methylthio)hepta-4,6-dien-3-ones and 9-phenyl-1,1-bis(methylthio)nona-4,6,8-trien-3-one followed by cycloaromatization of the resulting 3-substituted 1,1-bis(methylthio)alken-3-ols in the presence of boron trifluoride-diethyl ether complex.
ISSN:0039-7881
DOI:10.1055/s-1992-26305