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Thermal valence rearrangements of heterocycles, 3. A key aziridine intermediate of the Δ 4 ‐isoxazoline‐pyrrole rearrangement
Author(s) -
Mullen George B.,
Bennett Grace A.,
Georgiev Vassil St.
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900117
Subject(s) - chemistry , aziridine , pyrrole , cope rearrangement , valence (chemistry) , sigmatropic reaction , adamantane , rearrangement reaction , carroll rearrangement , stereochemistry , ring (chemistry) , photochemistry , organic chemistry , catalysis
Utilizing the spiro[adamantane‐Δ 4 ‐isoxazoline] precursor 10 , a key 2‐acylaziridine intermediate ( 11 ) has been isolated, thus providing conclusive evidence that an initial ring contraction may be considered to be the first step of the Δ 4 ‐isoxazoline‐pyrrole rearrangement.