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Generation of 2-lithio-2-(methylthio)-1,3-benzodithioles, new carboxyl carbanion equivalents, and their application to the syntheses of unsymmetrical hexathioorthooxalates

Brown, Charles Allan, Miller, Robert D., Lindsay, Charles M. and Smith, Keith 1984. Generation of 2-lithio-2-(methylthio)-1,3-benzodithioles, new carboxyl carbanion equivalents, and their application to the syntheses of unsymmetrical hexathioorthooxalates. Tetrahedron Letters 25 (9) , pp. 991-994. 10.1016/S0040-4039(01)80082-4

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Abstract

2-Lithio-2-(methylthio)-1,3-benzodithioles are readily generated either by thiophilic addition of methyllithium to o-phenylenetrithiocarbonates or by deprotonation of 2-(methylthio)- 1,3-benzodithioles with n-butyllithium in THF; these anions are protonated (aqueous NH4Cl) or methylated (MeI) as expected, but undergo an unexpected, overall carbophilic addition reaction with cyclic trithiocarbonates to yield, after alkylation, unsymmetrical hexathioorthooxalates, compounds which have been difficult to prepare by traditional methods.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Elsevier
ISSN: 0040-4039
Last Modified: 04 Jun 2017 02:57
URI: http://orca.cf.ac.uk/id/eprint/14531

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