The reaction of hydrogen chloride on 7-, 8(14)-, and 14-ene steroids was investigated. A 14α-chloro compound is the product of kinetically controlled addition of the acid. A 14β-chloro compound with the side chain in the 17α configuration originates in diethyl ether at temperatures lower than -30°C in the presence of hydrogen chloride, via a carbocation at C14. There is evidence that the inversion occurs through two distinct rearrangements involving the intermediary formation of a 12,14α-cyclo-12,13-seco-5α-cholest-13(17)-ene.
Side-chain inversion of steroidal olefins promoted by hydrogen chloride / M. Anastasia, A. Fiecchi, A. Scala. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 43:18(1978), pp. 3505-3508.
Side-chain inversion of steroidal olefins promoted by hydrogen chloride
M. AnastasiaPrimo
;
1978
Abstract
The reaction of hydrogen chloride on 7-, 8(14)-, and 14-ene steroids was investigated. A 14α-chloro compound is the product of kinetically controlled addition of the acid. A 14β-chloro compound with the side chain in the 17α configuration originates in diethyl ether at temperatures lower than -30°C in the presence of hydrogen chloride, via a carbocation at C14. There is evidence that the inversion occurs through two distinct rearrangements involving the intermediary formation of a 12,14α-cyclo-12,13-seco-5α-cholest-13(17)-ene.
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