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Triplet-Sensitized Photoreactivity of Geminal Diazidoalkane.
MedLine Citation:
PMID:  21894937     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Photolysis of 1 in chloroform yielded 2 as the major product and a small quantity of 3. Laser flash photolysis demonstrated that upon irradiation, the first excited triplet state of the ketone (T1K) of 1 is formed and decayed to form radical 4, which has a (lambda)max at 380 nm ((tau)=2(mu)s). Radical 4 expelled a nitrogen molecule to yield imine radical 5 ((lambda)max at 300 nm). Density functional theory (DFT) calculations showed that the transition state barrier for the formation of 5 is approximately 4 kcal/mol. In comparison, photolysis of 1 in argon matrices resulted in triplet nitrene 6, which was further characterized with 15N and D isotope labeling and DFT calculations. Prolonged irradiation of 6 yields triplet imine nitrene 7.
Authors:
Ranaweera A A Upul Ranaweera; Jagadis Sankaranarayanan; Lydia Casey; Bruce S Ault; Anna Dora Gudmundsdottir
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-9-6
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Sep 
Date Detail:
Created Date:  2011-9-7     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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