Document Detail

Stereocontrolled photodimerization with congested 1,8-bis(4'-anilino)naphthalene templates.
MedLine Citation:
PMID:  20809657     Owner:  NLM     Status:  MEDLINE    
Suzuki cross-coupling of a 1,8-dihalonaphthalene with 4-methoxy-3-methylphenylboronic acid or 4-acetamidophenylboronic acid and subsequent functional group transformation gave 1,8-bis(3'-methyl-4'-anilino)naphthalene, 16, and 1,8-bis(4'-anilino)naphthalene, 21, in 65% and 90% overall yield, respectively. These congested compounds exhibit two cofacial aniline rings that favor a proximate, parallel arrangement of covalently attached cinnamoyl units suitable for stereoselective photodimerization. The [2 + 2]cycloaddition was found to proceed with high yield and exclusive formation of cis,trans,cis-cyclobutane-1,2-dicarboxylic acids. Amide formation with cinnamoyl chloride and template 21 followed by photochemical dimerization and acidic hydrolysis gave β-truxinic acid, 10, in 69% overall yield. Coupling of 21 and (E)-3-(3,4-dimethylphenyl)acrylic acid in the presence of EDC, UV irradiation, and cleavage gave cis,trans,cis-3,4-bis(3,4-dimethylphenyl)cyclobutane-1,2-dicarboxylic acid, 26, in 60% yield. In both cases, the template was quantitatively recovered.
Marwan W Ghosn; Christian Wolf
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-09-24     Completed Date:  2011-01-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6653-9     Citation Subset:  IM    
Department of Chemistry, Georgetown University, Washington, DC 20057, USA.
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MeSH Terms
Crystallography, X-Ray
Hydrogen Bonding
Models, Molecular
Molecular Structure
Naphthalenes / chemical synthesis*,  chemistry
Reg. No./Substance:

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