A synthetic alternative to the type-II intramolecular 4 + 3 cycloaddition reaction

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7899-7902

  Grainger, Richard S ^a   Owoare, Richard B ^a   Tisselli, Patrizia ^a   Steed, Jonathan W ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OXYALLYL CATIONS;

ALKYLATION; POSITIVE IONS; REACTION KINETICS;

AROMATIC COMPOUNDS;

ALLYL COMPOUND; CATION; FLUORINE DERIVATIVE; HEXAFLUOROPROPAN 2 OL; SOLVENT; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLOADDITION; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141765909     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034356f     Document Type: Article

References (41)

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40. The author has deposited X-ray coordinates with the Cambridge Crystallographic Data Center (CCDC 202411).
41. Although determination of the optimal chain length between diene and oxyallyl cation was not the aim of this study, it may well be that other systems undergo the Type-II 4 + 3 cycloaddition with greater ease than 5 or 6. In this respect, it is perhaps notable that to the best of our knowledge Type-I intramolecular 4 + 3 cycloadditions are only known with three or four atoms in the tether to form five- or six-membered rings, respectively.