Stereodirecting effects in the characterization of ylide intermediates in reactions of singlet methylene with an allylic ether and an allylic chloride
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The stereodirecting effects of substrate substituents were examined in addition of 1:CH2 to the double bonds of 3-methoxycyclohexene (3a), 3-chlorocyclohexene (3b), and 3-methylcyclohexene (3c) in pentane solution at temperatures from 23°C to −50°C. A preference for addition syn to the directing substituent was observed in reactions of 3a and 3b and was attributed to a reversible interaction of carbene and substituent. In the reaction with 3a this interaction was not obviously ylide formation.
Cubbage, J. W., Edelbach, B. L., Kuen, K. S., & DeLuca, J. A. P. (1997). Stereodirecting Effects in the Characterization of Ylide Intermediates in Reactions of Singlet Methylene with an Allylic Ether and an Allylic Chloride. Tetrahedron, 53(29), 9823–9834. https://doi.org/10.1016/s0040-4020(97)00329-3
© 1997 Elsevier Science Ltd.