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A Novel Nitrone Cycloaddition/Rearrangement
Author(s) -
Toder Bruce H.,
Mullen George B.,
St. Georgiev Vassil
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730119
Subject(s) - chemistry , nitrone , oxaziridine , toluene , tetrahydrofuran , cycloaddition , fragmentation (computing) , organic chemistry , medicinal chemistry , stereochemistry , solvent , catalysis , computer science , operating system
Adamantanone‐derived nitrone 4 and some other keto‐nitrones, when reacted with aromatic and aliphatic aldehydes in refluxing toluene or tetrahydrofuran, formed the corresponding aldonitrones ( Z )‐ 10 , the latter arising from the fragmentation of an initially formed 1 , 4 , 2 ‐dioxazolidine 6 to adamantan‐2‐one and an oxaziridine intermediate 11 , which then rearranges to ( Z )‐ 10 .