Photolysis of α-Azidoacetophenones:  Trapping of Triplet Alkyl Nitrenes in Solution

Selective excitation of the ketone chromophore in α-azidoacetophenones, 1, leads to intramolecular triplet energy transfer to the azido group, which forms the corresponding triplet alkyl nitrene, 2. Azides 1 also undergo α-cleavage to form benzoyl and methyl azido radicals in competition with nitren...

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Bibliographic Details
Published inOrganic letters Vol. 3; no. 4; pp. 523 - 526
Main Authors Mandel, Sarah M, Krause Bauer, Jeanette A, Gudmundsdottir, Anna D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.02.2001
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RESOLVED INFRARED-SPECTROSCOPY
METHYLNITRENE
PHENYL AZIDE
ACYL RADICALS
SINGLET
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Summary:Selective excitation of the ketone chromophore in α-azidoacetophenones, 1, leads to intramolecular triplet energy transfer to the azido group, which forms the corresponding triplet alkyl nitrene, 2. Azides 1 also undergo α-cleavage to form benzoyl and methyl azido radicals in competition with nitrene formation. Thus the major photoproduct, 2-benzoylamino-1-phenylethanone, 3, comes from trapping of 2 with a benzoyl radical. This appears to be the first observation of bimolecular trapping of triplet alkyl nitrenes in solution.
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SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0068750