G. V. Boyd, T. Norris, P. Lindley
1976
Citations
0
Influential Citations
14
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
The title compounds [(3a), (11), and (15a)] were obtained from dehydrodithizone and, respectively, 1-diethylaminopropyne, the morpholine enamine of 1-methyl-4-piperidone, and 2-pyrrolidinoindene, and their structures were determined by single-crystal X-ray structure analysis. Likewise, reaction of dehydrodithizone with 1-dimethylamino-2-phenylacetylene gave the phenylazopyrazole (3c), with β-piperidinostyrene the phenylazo-1,3,4-thiadiazine (12), and with 2-piperidino- and 2-morpholino-indene the phenylazospiro[indene-[1,3,4]thiadiazoles](15b and c). In contrast, dimethyl acetylenedicarboxylate and tetraphenylcyclopentadienone formed 1,3-dipolar cycloadducts, which are formulated as the thiazolo[3,2-d]tetrazoles (4) and (5)[or (6)], respectively. The different modes of behaviour of dehydrodithizone towards electron-rich and electron-poor components are rationalized by means of frontier-orbital theory.