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Isotopic labeling as a probe in the study of a degenerate Payne Rearrangement in a tertiary epoxide system
Author(s) -
Bajwa Joginder S.,
Sunay Ustun B.
Publication year - 1997
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199709)39:9<787::aid-jlcr19>3.0.co;2-2
Subject(s) - epoxide , chemistry , carroll rearrangement , medicinal chemistry , stereochemistry , sigmatropic reaction , photochemistry , organic chemistry , catalysis
Through the use of isotropic labeling, it has been shown that epoxide 6 undergoes Payne Rearrangement under basic protic conditions (NaOD/D 2 O/rt). However, no rearrangement took place when epoxide 6 was exposed to basic aprotic conditions (NaH/THF/reflux). © 1997 John Wiley & Sons, Ltd.