Intramolecular sulfur ylide additions to ketones

JK Crandall, HS Magaha, MA Henderson…

Index: Crandall, Jack K.; Magaha, H. Steve; Henderson, Mark A.; Widener, Rexford K.; Tharp, Gregg A. Journal of Organic Chemistry, 1982 , vol. 47, # 27 p. 5372 - 5380

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Citation Number: 21

Abstract

Methodology is described for the annulation of five-membered carboxylic rings onto cycloalkanones, using an intramolecular sulfur ylide reaction. Epoxybicyclo [x. 3.0] alkanes (x= 3, 4, 5, 6) were obtained from cycloalkanones via the corresponding 2-[3-(phenylthio) propyl] cycloalkanones (Za-d, 7, 1 I), which were reacted successively with triethyloxonium tetrafluoroborate and potassium tert-butylate. An analogous annulation to give a six- ...