Journal of the American Chemical Society

Effect of the silicon site on the cyclization of sila-5-hexen-1-yl radicals. The unusual effect of. alpha.-silicon

JW Wilt

Index: Wilt, James W. Journal of the American Chemical Society, 1981 , vol. 103, # 17 p. 5251 - 5253

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Citation Number: 40

Abstract

A representative procedure for the intramolecular Diels-Alder reaction of o-quinone methide N-alkenylimine intermediate (6) is exemplified by the synthesis of benzo [c] quinolizidine (7b). To a refluxing suspension of 304 mg (2 mmol) of CsF in 10 mL of acetonitrile, a solution of 400 mg (1 mmol) of [o-[(trimethylsilyl) hex-5-enylamino] benzyl] trimethylammonium bromide (9)'in 10 mL of acetonitrile was added dropwise over 1 h and then heated at ...