A Novel Nitrone Cycloaddition/Rearrangement | Zendy

Toder Bruce H. | Zendy; Mullen George B. | Zendy; St. Georgiev Vassil | Zendy

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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 .

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