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Photoarylation/alkylation of bromonaphthols.
MedLine Citation:
PMID:  19123847     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The photochemistry of 6-bromo-2-naphthols has been studied in acetonitrile, aqueous acetonitrile, and isopropyl alcohol in the absence and in the presence of triethylamine by product distribution analysis, laser flash photolysis (LFP), fluorescence, phosphorescence, electrochemical measurements, and DFT calculations. Hydrobromic acid loss in the presence of Et(3)N occurs from the triplet state of 6-bromo-2-naphthol, generating an electrophilic carbene intermediate, which has been successfully trapped by oxygen, allyltrimethylsilane, 2,3-dimethylbut-2-ene, pyrrole, acrylonitrile, 1,4-dimethoxybenzene, and also pyridine. The generation and the reactivity of a triplet carbene intermediate has been supported by LFP, with the detection of 2,6-naphthoquinone-O-oxide (530 < lambda < 650 nm) in the presence of O(2). The electrophilic diradical character of the carbene has been supported by DFT calculations, using the B3LYP, PBE0, and MPWB1K functionals, with the 6-31+G(d,p) basis set and PCM solvation model.
Authors:
Luca Pretali; Filippo Doria; Daniela Verga; Antonella Profumo; Mauro Freccero
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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 Feb 
Date Detail:
Created Date:  2009-01-30     Completed Date:  2009-06-23     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1034-41     Citation Subset:  -    
Affiliation:
Dipartimento di Chimica Organica, Universita di Pavia, 27100 Pavia, Italy.
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