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Conjugation of spirocyclopropane with the carbonyl group. Conformational analysis of spiro [cyclopropane‐1,2′‐steroids]
Author(s) -
Desai Umesh R.,
Trivedi Girish K.
Publication year - 1991
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260290210
Subject(s) - chemistry , cyclopropane , ring (chemistry) , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , organic chemistry
The conjugative ability of a spirocyclopropane on 4‐en‐3‐one steroids was studied with the help of 13 C NMR and two‐dimensional experiments such as COSY and NOESY. The conformational analysis of the A ring of these compounds indicates a ‘normal’ (1α,2β)‐ half‐chair conformation rather than the expected ‘inverted’ (1β,2α)‐ half‐chair conformation. Application of the modified McConnell equation for the shielding influence of the cyclopropane aids the analyses.