Synthesis of cis,cis,cis-Tetrasubstituted Cyclobutanes. Trapping of Tetrahedral Intermediates in Intramolecular Nucleophilic Addition

The intramolecular [2 + 2] photocycloaddition of bismaleimides leads to cage diimides 2. Nucleophilic addition on these compounds (NaBH4, RLi, or MeONa) gives rise to various diazatetracyclic 4 and 11 or oxadiazapentacyclic 3 “bowl shaped” alcohols. X-ray analyses of 3c and 11a provide definite stru...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-10, Vol.65 (20), p.6418-6422
Main Authors: Laurenti, Dorothée, Santelli-Rouvier, Christiane, Pèpe, Gérard, Santelli, Maurice
Format: Article
Language:English
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Summary:The intramolecular [2 + 2] photocycloaddition of bismaleimides leads to cage diimides 2. Nucleophilic addition on these compounds (NaBH4, RLi, or MeONa) gives rise to various diazatetracyclic 4 and 11 or oxadiazapentacyclic 3 “bowl shaped” alcohols. X-ray analyses of 3c and 11a provide definite structural data concerning these two highly functionalized compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000361x