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1 H and 13 C studies of alkenes, epoxides and cyclic thionocarbonates
Author(s) -
Hevesi L.,
Nagy J. B.,
Krief A.,
Derouane E. G.
Publication year - 1977
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270100105
Subject(s) - stereospecificity , chemistry , ring (chemistry) , alkyl , stereochemistry , cis–trans isomerism , complement (music) , organic chemistry , biochemistry , complementation , gene , phenotype , catalysis
1 H and 13 C chemical shift data are presented and discussed for a number of di‐ and tri‐alkyl substituted alkenes, epoxides and thionocarbonates. The completely stereospecific interconversion of these compounds, together with the n.m.r. data, allows a straightforward and quantitative stereochemical analysis. For 1 H n.m.r., the most useful intermediates proved to be the thionocarbonates. The differential shieldings between cis and trans isomers are tentatively explained in terms of the conformational change of the 5‐membered thionocarbonate ring. In 13 C n.m.r., either series can be useful to distinguish between stereoisomers. The conclusions stemming from the 13 C n.m.r. results complement the 1 H n.m.r. studies.