Document Detail


Quantitative analyses of mixtures of 2-deuterio-1-vinylcyclobutanes.
MedLine Citation:
PMID:  19757797     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Making distinctions between two stereoisomers characterized by diastereotopic deuterium atoms can ordinarily be achieved using standard NMR spectroscopic methods. Mixtures of stereoisomers having both diastereotopic and enantiotopic deuterium labels, however, may be difficult to analyze quantitatively. The present work introduces a simple way to gain quantitative analyses of mixtures of the four stereoisomeric 2-deuterio-1-vinylcyclobutanes, an essential prerequisite to establishing the stereochemical characteristics of the thermal stereomutations of vinylcyclobutane and its structural isomerizations to cyclohexene. The unconventional NMR method introduced and validated in this work will likely prove convenient and generally applicable to related stereochemical investigations.
Authors:
John E Baldwin; David J Kiemle; Alexey P Kostikov
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  74     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2009 Oct 
Date Detail:
Created Date:  2009-10-09     Completed Date:  2009-12-29     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7866-72     Citation Subset:  -    
Affiliation:
Department of Chemistry, Syracuse University, Syracuse, New York 13244, USA. jbaldwin@syr.edu
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