A New General Route to 1,2-Diarylethylenes, 1,4-Diarylbutadienes and 1,6-Diarylhexatrienes Through Cycloaromatization of β-Oxodithioacetals

Ch. Srinivasa Rao; Okram M. Singh; Hiriyakkanavar Ila; Hiriyakkanavar Junjappa

doi:10.1055/s-1992-26305

Synthesis 1992; 1992(11): 1075-1077
DOI: 10.1055/s-1992-26305

short paper

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A New General Route to 1,2-Diarylethylenes, 1,4-Diarylbutadienes and 1,6-Diarylhexatrienes Through Cycloaromatization of ß-Oxodithioacetals

Ch. Srinivasa Rao^* , Okram M. Singh, Hiriyakkanavar Ila, Hiriyakkanavar Junjappa

^*Department of Chemistry, North-Eastern Hill University, Shillong - 793 003, Meghalaya, India

Abstract

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A new general route for the title olefins 5a-e, 12, 13, 8a-e and 11a-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.

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