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The unusual formation of methyl alpha-(5,6-dimethoxycarbonyl-2,3-dimethoxyazepin-7-ylidene)-alpha-[5-methoxycarbonyl-2,3-dimethoxypyrid-6-yl)acetate during the pyrolysis of ''azido-meta-hemipinate'' - First example of a reaction involving a concomitant ring expansion and ring extrusion

Eswaran, SV and Neela, HY and Ramakumar, S and Viswamitra, MA (1996) The unusual formation of methyl alpha-(5,6-dimethoxycarbonyl-2,3-dimethoxyazepin-7-ylidene)-alpha-[5-methoxycarbonyl-2,3-dimethoxypyrid-6-yl)acetate during the pyrolysis of ''azido-meta-hemipinate'' - First example of a reaction involving a concomitant ring expansion and ring extrusion. In: Journal of Heterocyclic Chemistry, 33 (4). 1333-1337 .

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/jhet.55...

Abstract

he ortho methoxycarbonyl substituent constitutes a sole exception in the ring closure reactions of ortho substituted aryl azides, as it provides no rate acceleration to this reaction. Pyrolysis of ''azido-meta-hemipinate'', an aryl azide containing such a substituent, led us to the title compound, a new azepinylidenepyridylacetic ester, whose structure has been established unambiguously by a single crystal X-ray diffraction study. This is the first report of a reaction involving both a ring expansion to an azaheptafulvalene and a ring extrusion to a pyridyl ring residue.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Journal of Heterocyclic Chemistry.
Department/Centre: Division of Physical & Mathematical Sciences > Physics
Date Deposited: 13 May 2011 07:02
Last Modified: 13 May 2011 07:02
URI: http://eprints.iisc.ernet.in/id/eprint/37641

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