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Computational study of the thermal rearrangement of acetoxy(methoxy)carbene
Author(s) -
Czardybon Wojciech,
Warkentin John,
Werstiuk Nick Henry
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.899
Subject(s) - carbene , chemistry , thermal decomposition , cope rearrangement , concerted reaction , sigmatropic reaction , photochemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Thermolysis of 2‐acetoxy‐2‐methoxy‐5,5‐dimethyl‐Δ 3 ‐1,3,4‐oxadiazoline affords acetoxy(methoxy)carbene. Thermal rearrangement of acetoxy(methoxy)carbene to methyl pyruvate is a concerted 1,2‐migration, avoiding a potential radical‐pair mechanism. Copyright © 2005 John Wiley & Sons, Ltd.