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.
Titolo: | Side-chain inversion of steroidal olefins promoted by hydrogen chloride | |
Autori: | ANASTASIA, MARIO (Primo) | |
Settore Scientifico Disciplinare: | Settore BIO/10 - Biochimica | |
Data di pubblicazione: | 1978 | |
Rivista: | ||
Tipologia: | Article (author) | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/jo00412a019 | |
Appare nelle tipologie: | 01 - Articolo su periodico |