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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 9
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Original Articles

Base-Catalyzed Decomposition of Acena Phtheneouinone Bissulfonylhydrazones to 1,8-Dicyanonaphthalenes, the Presumed Thermal Chemistry of 1,2,3,4-Tetrazine

Pages 673-680 | Published online: 05 Dec 2006
 

Abstract

In the course of our investigation of the chemistry of diazoacenaphthene, we needed 2-benzylidene-1-diazoacenaphthene (2). As a possible precursor to 2, benzylideneacenaphthenone (1) was treated with one equivalent of tosylhydrazine with the expectation that 2 would be formed following basic decomposition. Surprisingly, acenaphthenequinone bistosylhydrazone (3) was produced instead (Eq. 1).

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