Unsaturated macrocyclic compounds. 122. Synthesis of methyl-substituted bisdehydro [13] annulenones. Conformational isomerism and ring current effects in …

TM Cresp, J Ojima, F Sondheimer

Index: Cresp,T.M. et al. Journal of Organic Chemistry, 1977 , vol. 42, p. 2130 - 2134

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Citation Number: 47

Abstract

137 mL of toluene was heated at reflux under nitrogen for 5 h. After cooling, the solvent was evaporated at reduced pressure to give an oil. 1H NMR analysis of the crude reaction mixture showed that the reaction had proceeded with a ca. 40% conversion of the starting dienone to give a quantitative yield of 10. Most of the dienone was removed by distillation (55" C, 0.03 mm). U pon extended standing, sulfoxide 10 slowly crystallized from the ...