Issue 0, 1986
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Vinyl azides in heterocyclic synthesis. Part 3. Isolation of azirine trimers (1,3,8-triazatricyclo[4.3.0.03,5]non-7-enes) and intramolecular interception of nitrile ylides by neighbouring π-bonds or nucleophiles

Deirdre M. B. Hickey,   Christopher J. Moody  and  Charles W. Rees  

Abstract

Photolysis of azidocinnamates (1a–e) at 300 nm in light petroleum gives exclusively the triazatricyclononenes (7a–e) in a highly stereospecific trimerisation of the corresponding azirine (2). A mechanism is proposed involving the sequence: azide (1)→ azirine (2)→ nitrile ylide (8)→ dimer (9)→ azomethine ylide (10)→ trimer (7)(Scheme 2). This mechanism not only rationalizes the formation of the trimers (7), rather than dimers or oligomers, but also their stereochemistry. Further evidence for it is provided by photolyses of the azidocinnamates (1f–h) which give the ‘dimer’(13), the cyclopropaisoquinoline (16), and the imidazopyridine (20), respectively; these three products result from intramolecular interception of the azomethine ylide or nitrile ylide intermediates.

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Article information

DOI
https://doi.org/10.1039/P19860001119
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122

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Vinyl azides in heterocyclic synthesis. Part 3. Isolation of azirine trimers (1,3,8-triazatricyclo[4.3.0.03,5]non-7-enes) and intramolecular interception of nitrile ylides by neighbouring π-bonds or nucleophiles

D. M. B. Hickey, C. J. Moody and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1986, 1119 DOI: 10.1039/P19860001119

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