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13C, 1H long-range coupling constants in configuration assignment of some trisubstituted alkenes

✍ Scribed by Peter Fischer; Eberhard Schweizer; Jörg Langner; Ulrich Schmidt

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
158 KB
Volume
32
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Chemical shifts and long‐range ^13^C, ^1^H coupling constants to the two carbonyl C atoms were determined for a series of ethyl 2‐acyloxy‐2‐alkenoates. The ^3^J(C,H) coupling constant across the double bond is 9.5–10.1 Hz for the E‐ and 2.9–3.8 Hz for the Z‐isomer. ^3^J(C,H) values, therefore, may be used as a criterion for E/Z differentiation even if only one isomer is available. ^13^C chemical shift data, in contrast, cannot be employed for a straightforward differentiation.

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