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Advances in Heterocyclic Chemistry, Vol. 34 - download pdf or read online

By Alan R. Katritzky (ed.)

ISBN-10: 012020634X

ISBN-13: 9780120206346

Meant for natural chemists, this quantity follows the structure of earlier volumes and offers up to date info on chosen parts of heterocyclic chemistry.

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Extra info for Advances in Heterocyclic Chemistry, Vol. 34

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Janiga, and J . F. Lorenc. J. Org. Chem. 42, 3721 (1977). J . P. Freeman and E. R . Janiga, J. Org. Chem. 39, 2663 (1974). W. R . Dolbier, Jr. and W. M. S. Chem. , 289 (1970). R . Paredes and W. R . , Rev. Latinoam. Quim. 6, 29 (1975) [CA 83, 8773p ( 1975)). 26 [Sec. H MICHAEL P. SAMMES AND ALAN R. KATRITZKY 2. Il8 Hypobromite oxidation of 97 leads to the same compound’29(Scheme 3 9 , whereas the 4-bromo analog of 96 has been prepared by base elimination of HBr from a dibromopyrazoline N,N’-dioxide p r e c u r ~ o r .

I6' Other inter- and intramolecular reactions of the carbenes are discussed in the next section. c. Steps 111 and 111': the Fate of the Carbene. When photolysis is conducted in an inert solvent, the major process is insertion of the carbene into the double bond to give a cyclopropene (Step 111, Scheme 56), unless an alternative, energetically favorable, reaction pathway (Step 111') exists. The most important of these is indene formation. '''*1'2The intramolecular nature of the hydride shift was established by lack of exchange with deuterium in the solvent.

C. Dietrich-Buchecker and M. Franck-Neumann, Tetrahedron 33, 751 (1977). M. Franck-Neumann and C . Dietrich-Buchecker, Terruhedron 34, 2797 (1978). 44 [Sec. B MICHAEL P. SAMMES AND ALAN R. I6' Other inter- and intramolecular reactions of the carbenes are discussed in the next section. c. Steps 111 and 111': the Fate of the Carbene. When photolysis is conducted in an inert solvent, the major process is insertion of the carbene into the double bond to give a cyclopropene (Step 111, Scheme 56), unless an alternative, energetically favorable, reaction pathway (Step 111') exists.

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Advances in Heterocyclic Chemistry, Vol. 34 by Alan R. Katritzky (ed.)


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