The Journal of Organic Chemistry

Metal-ammonia reduction. XI. Regiospecific and stereoselective reduction in the chrysene series

RG Harvey

Index: Harvey,R.G. Journal of Organic Chemistry, 1971 , vol. 36, # 22 p. 3306 - 3311

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Citation Number: 12

Abstract

Metal-ammonia reduction of chrysene through the hexahydro stage proceeds regiospecifically via 5, 6-dihydro-(1) and 4b, 5, 6, 12-tetrahydro-(2) to 4b, 5, 6, 10b, 11, 12- hexahydrochrysene (3). Existence in liquid ammonia of stable monoanionic intermediates related to 1 and 2, but not 3, is demonstrated by reductive methylation. Cis stereoselectivity observed in reduction of both 2 and 5, 6, 11, 12-tetrahydrochrysene to 3 is dependent ...