Stereoelectronic control in the photorearrangement of. alpha.-chloro ketones. Mechanistic studies in photochemistry. XIII

RS Givens, L Strekowski

Index: Givens,R.S.; Strekowski,L. Journal of the American Chemical Society, 1975 , vol. 97, p. 5867 - 5873

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Citation Number: 5

Abstract

Abstract: The photorearrangement of anti-and syn-2-chlorobenzobicyclo [2.2. 2] octadien-3- one(1 and 2) in methanol gave naphthalene, methyl 1-naphthylacetate (6) and 7- carbomethoxy-2, 3-benzonorcaradiene (5). The photolysis of anti-2-chloro-bicyclo [2.2. 2] octen-3-one (3) gave the 7-carbomethoxynorcarene (7) in 55% yield. The corresponding syn- chloro ketone (4) did not rearrange to the norcarene product illustrating the ...