Protium–deuterium exchange of 17-oxosparteine: Homoenolization of a lactam Academic Article uri icon

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abstract

  • The H–D exchange of 17-oxosparteine (1b) has been studied under homoenolization conditions. We find that 1b undergoes H–D exchange at the bridgehead carbon C7 at 130 °C, but forcing conditions (240 °C) using the medium (CD3)3COK/(CD3)3COD are required to induce exchange at C11, C15, and other sites. C15-Ha exchanges only marginally faster than C15-Hc, indicating that the β-lactam carbanion is stabilized primarily by the dipolar effect of the amide group. Keywords: protium–deuterium exchange, 17-oxosparteine, homoenolization.

publication date

  • March 1, 1989