Molecular Structures of syn- and anti-20-carboethoxyhydrazone isomers of 3Β, 21-diacetoxypregna-5,16-dien-20-one

Authors

Sergey Lindeman, Marquette UniversityFollow
A. M. Turuta, A. N. Nesmeyanov Institute of Organometallic CompoundsAcademy of Sciences of the USSRFollow
Yuri T. Struchkov, A. N. Nesmeyanov Institute of Organoelemental CompoundsAcademy of Sciences of the USSRFollow
A. V. Kamernitskii, A. N. Nesmeyanov Institute of Organometallic CompoundsAcademy of Sciences of the USSRFollow

Document Type

Article

Language

eng

Publication Date

3-1991

Publisher

Springer

Source Publication

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science

Source ISSN

0020-1693

Abstract

The validity of syn- and anti-isomer assignments in the case of 3Β,21-diacetoxypregna-5, 16-dien-20-one 20-carboethoxyhydrazones has been established by x-ray structural analysis; the isomer designations had been made previously based on chemical and spectral data. The isomers differ sharply in the conjugative relationship between the hydrazone group and the C¹⁶=C¹⁷ double bond in the steroid skeleton: the syn-isomer is trans-conjugated (the degree of twisting about the C¹⁷-C²⁰ bond is characterized by a torsional angleψ=-161.0‡), while the anti-isomer is not conjugated (ϕ=− 75.3‡); this explains the electronic spectral features of these isomers.

Comments

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, Vol. 40, No. 3 (March 1991): 529-533. DOI.

Sergey Lindeman was affiliated with A. N. Nesmeyanov Institute of Organometallic CompoundsAcademy of Sciences of the USSR at the time of publication.

Recommended Citation

Lindeman, Sergey; Turuta, A. M.; Struchkov, Yuri T.; and Kamernitskii, A. V., "Molecular Structures of syn- and anti-20-carboethoxyhydrazone isomers of 3Β, 21-diacetoxypregna-5,16-dien-20-one" (1991). Chemistry Faculty Research and Publications. 720.
https://epublications.marquette.edu/chem_fac/720