The Chemistry of α-Oxo Ketene Cyclic Dithioacetals(Ⅳ)——Studies on the Dehydration of Adducts of β,β-1,3-Propylene-dithio-α,β-Unsaturated Arylketones with Allyl Grignard Reagents

Chem. J. Chinese Universities ›› 1993, Vol. 14 ›› Issue (3): 353.

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The Chemistry of α-Oxo Ketene Cyclic Dithioacetals(Ⅳ)——Studies on the Dehydration of Adducts of β,β-1,3-Propylene-dithio-α,β-Unsaturated Arylketones with Allyl Grignard Reagents

LIU Qun¹, DONG De-Wen¹, YANG Zhi-Yun¹, HU Yu-Lan¹, JING Feng-Ying², XIAO Yan-Wen²

1. Dept.of Chem., Northeast Normal Univ., Changchun, 130024;
2. Changchun Institute of Afflied Chemistry, Academia Sinica, Changchun

Received:1992-07-20 Revised:1992-11-16 Online:1993-03-24 Published:1993-03-24

Abstract

Abstract: Anew route for the synthesis of dialkylthio conjugated alkenes (3) has been developed.The addition of β,β-l,3-propylenedithio-α,β-unsaturated arylketones (1) with allyl or benzyl Grig-nard reagents afforded the carbinols (2).The carbinols (2) were converted to the alkenes (3) via dehydration catalyzed by BF₃·Et₂O.The course of addition of benzyl Grignard reagents to (1) proceeds by regiospecific 1,2-pattern other than the sequential 1,4-, 1,2-addition, which might result from the hindrance of the rigid cyclic dithioalkyl group in (1), the mechanism and reaction condition are discussed.Thirteen new compounds are prepared, their structure are assigned by ¹H NMR, IRand UV.

Key words: β,β-1,3-Propylenedithio-α,β-unsaturated arylketones, Allyl Grignard reagent, Dehydration

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LIU Qun, DONG De-Wen, YANG Zhi-Yun, HU Yu-Lan, JING Feng-Ying, XIAO Yan-Wen. The Chemistry of α-Oxo Ketene Cyclic Dithioacetals(Ⅳ)——Studies on the Dehydration of Adducts of β,β-1,3-Propylene-dithio-α,β-Unsaturated Arylketones with Allyl Grignard Reagents[J]. Chem. J. Chinese Universities, 1993, 14(3): 353.

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The Chemistry of α-Oxo Ketene Cyclic Dithioacetals(Ⅳ)——Studies on the Dehydration of Adducts of β,β-1,3-Propylene-dithio-α,β-Unsaturated Arylketones with Allyl Grignard Reagents

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