The photolysis of C-nitroso-compounds. Part 8. The solution photolysis of some tertiary C-nitroso-compounds

Derek Forrest, Brian G. Gowenlock, Josef Pfab

Research output: Contribution to journalArticle

Abstract

The photolysis of the nitrosoalkanes 2-methyl-2-nitrosopropane (I), 2-nitroso-2-phenylpropane (II), 2-benzyl-2-nitrosopropane (III), and 1-nitrosoadamantane (IV) with visible light (? > 540 nm) yielded trialkylhydroxylamines and, with the exception of (IV), alkenes as main products. In methanol the alcohols, alkyl nitrites, and methyl nitrite were obtained additionally. These products are rationalised on the basis of a homolytic dissociation into a free radical and nitric oxide in the primary step. The reaction of nitric oxide with the substrate rather than a direct photoelimination of HNO is identified as the major source of alkenes.

Original languageEnglish
Pages (from-to)576-580
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
Publication statusPublished - 1979

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Nitroso Compounds
Photolysis
Alkenes
Nitric Oxide
Free Radicals
Methanol
Alcohols
Substrates
tert-nitrosobutane
cumene
methyl nitrite
1-nitrosoadamantane

Cite this

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abstract = "The photolysis of the nitrosoalkanes 2-methyl-2-nitrosopropane (I), 2-nitroso-2-phenylpropane (II), 2-benzyl-2-nitrosopropane (III), and 1-nitrosoadamantane (IV) with visible light (? > 540 nm) yielded trialkylhydroxylamines and, with the exception of (IV), alkenes as main products. In methanol the alcohols, alkyl nitrites, and methyl nitrite were obtained additionally. These products are rationalised on the basis of a homolytic dissociation into a free radical and nitric oxide in the primary step. The reaction of nitric oxide with the substrate rather than a direct photoelimination of HNO is identified as the major source of alkenes.",
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The photolysis of C-nitroso-compounds. Part 8. The solution photolysis of some tertiary C-nitroso-compounds. / Forrest, Derek; Gowenlock, Brian G.; Pfab, Josef.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 5, 1979, p. 576-580.

Research output: Contribution to journalArticle

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T1 - The photolysis of C-nitroso-compounds. Part 8. The solution photolysis of some tertiary C-nitroso-compounds

AU - Forrest, Derek

AU - Gowenlock, Brian G.

AU - Pfab, Josef

PY - 1979

Y1 - 1979

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