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Transformations of the dihydropyridine ring system.

Allgrove, Robery Charles. (1968) Transformations of the dihydropyridine ring system. Doctoral thesis, University of Surrey (United Kingdom)..

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Abstract

The reaction of a 4-chloromethyl-1,4-dihydropyridine with potassium cyanide has been investigated, and in this respect it has been found to behave analogously to other 4-chloromethyl-1,4-dihydropyridines. However, on treatment with water, a unique transformation, affording a dihydrofuran, demonstrated that the 4-chloromethyl-1,4-dihydropyridine was considerably more reactive than the other 4-chloromethyl-1,4-dihydro-pyridines which did not undergo analogous transformations. An attempt to rationalize this has been made, and a mechanism suggested for the formation of the 2,3-dihydrofuran. Evidence for the structure of the 2,3-dihydrofuran is presented. Some reactions of the compound have been investigated, including rearrangement to a fulvene derivative and degradation to 3,3-diacetylpropionaldehyde. The tautomerism of the latter compound is discussed in detail, and a synthesis described.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
NameEmailORCID
Allgrove, Robery Charles.
Date : 1968
Contributors :
ContributionNameEmailORCID
http://www.loc.gov/loc.terms/relators/THS
Additional Information : Thesis (Ph.D.)--University of Surrey (United Kingdom), 1968.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 13:56
Last Modified : 06 Nov 2018 16:53
URI: http://epubs.surrey.ac.uk/id/eprint/847682

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