Investigation of the scope and regiochemistry of alkynylboronate cycloadditions with sydnones

Journal of the American Chemical Society

Volumn 131, Issue 22, 2009, Pages 7762-7769

  Browne, Duncan L ^b   Vivat, Jérôme F ^b   Plant, Andrew ^c,d   Gomez Bengoa, Enrique ^a   Harrity, Joseph P A ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

^c JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

^d SYNGENTA CROP PROTECTION AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ESTERS; CYCLOADDITIONS; DFT METHOD; PYRAZOLE; REGIOCHEMICAL; REGIOCHEMISTRY; REGIOSELECTIVE METHOD; SYDNONES;

ESTERS; SYNTHESIS (CHEMICAL);

CYCLOADDITION;

BORONIC ACID DERIVATIVE; PYRAZOLE DERIVATIVE; SYDNONE DERIVATIVE; ALKYNE; FUSED HETEROCYCLIC RINGS;

ARTICLE; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; METHODOLOGY; SUBSTITUTION REACTION; SYNTHESIS; THEORY; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION;

ALKYNES; BICYCLO COMPOUNDS, HETEROCYCLIC; BORONIC ACIDS; CYCLIZATION; MODELS, MOLECULAR; PYRAZOLES;

EID: 67650555655     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902460n     Document Type: Article

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64. The observation that the strongly electron-withdrawing p-nitrophenyl group does not affect the reaction regioselectivity is intriguing and may reflect its symmetrical positioning with respect to the C- and N-reacting centers of the sydnone. In addition, the fact that this group is not directly involved in the cycloaddition process may explain its negligible effect on charge transfer values. We thank one of the referees for these suggestions.