Document Detail


The importance of the ene reaction for the C(2)-C(6) cyclization of enyne-allenes.
MedLine Citation:
PMID:  11389639     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The present study establishes the ene reaction as a competing reaction mechanism to the diradical mechanism for the thermal C(2)-C(6) cyclization of enyne-allenes which possess bulky substituents at the alkyne terminus. Both reaction routes are found to possess nearly equal free energies of activation. As shown by our computations, primary H/D isotope effects could be used for a definite decision about the mechanism. Concerning the regioselectivity of the cyclization reactions of enyne-allenes our study resolves a long-standing deviation between theoretical results and experimental findings.
Authors:
P W Musch; B Engels
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  123     ISSN:  0002-7863     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2001 Jun 
Date Detail:
Created Date:  2001-06-06     Completed Date:  2001-12-28     Revised Date:  2003-10-31    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5557-62     Citation Subset:  -    
Affiliation:
Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.
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