Helvetica Chimica Acta

The Carbonyl Group as Homoconjugated Electron??Releasing Substituent. Regioselective electrophilic additions at bicyclo [2.2. 1] hept??5??en??2??one, bicyclo [2.2. 2] …

PA Carrupt, P Vogel

Index: Carrupt, Pierre-Alain; Vogel, Pierre Helvetica Chimica Acta, 1989 , vol. 72, p. 1008 - 1028

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Citation Number: 26

Abstract

Abstract In CHCl 3, CH 3 CN, or AcOH, benzeneselenenyl chloride (PhSeCl), bromide (PhSeBr), and acetate (PhSeOAc), 2-nitrobenzenesulfenyl chloride (NO 2 C 6 H 4 SCl), and 2, 4-dinitrobenzenesulfenyl chloride ((NO 2) 2 C 6 H 3 SCl) added to bicyclo [2.2. 1] hept-5- en-2-one (5) in an. anti fashion with complete stereo-and regioselectivity, giving adducts 20– 24 in which the chloride, bromide, or acetoxy substituent (X) occupies the endo position at ...