Intra-and intermolecular cyclization of olefinic tosylhydrazones under acidic conditions. A facile synthesis of bicyclic azoalkanes

…, JW Rekers, AB Packard, RC Elder

Index: Wilson, R. Marshall; Rekers, John W.; Packard, Alan B.; Elder, R. C. Journal of the American Chemical Society, 1980 , vol. 102, # 5 p. 1633 - 1641

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Citation Number: 29

Abstract

Abstract: Tosylhydrazones of olefinic ketones and aldehydes have been observed to undergo a variety of unusual cyclizations under acidic conditions. The intramolecular version of this novel cyclization reaction has been applied in the synthesis of previously unaccessible bicylo [3.2. I]-and bicyclo [2.2. 1 Jazoalkanes. Of these two bicyclic systems, the less strained [3.2. 1 J system is formed with the greater ease, and in either system the ...