Regioselectivity of rhodium (II)-catalyzed decomposition of 1-alkyl-1-(diazoacetyl) alkenes. Synthesis of 2-alkyl-2-cyclopentenones and 2-alkylidenecyclopentanones

P Ceccherelli, M Curini, MC Marcotullio…

Index: Ceccherelli, Paolo; Curini, Massimo; Marcotullio, Maria Carla; Rosati, Ornelio; Wenkert, Ernest Journal of Organic Chemistry, 1991 , vol. 56, # 25 p. 7065 - 7070

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Citation Number: 11

Abstract

Conclusion Several facta emerge from the above reaction results. Cyclopentenone formation (loa, 1 la and 12a) is the sole consequence of the cabon-hydrogen insertions of l- (dia-zoacety1)-l-ethylalkenes (4g, 8g, and 9g), Le., the y center adjacent to the olefinic bond shows much higher reactivity toward the carbenoid moiety than the methyl group of the saturated two-carbon side chain. Cyclopentenones (loa, llb, and 12c) are the preferred ...