ISSN:
0947-3440
Keywords:
1,2-Dithiin
;
Cycloadditions
;
Sulfur extrusion
;
Thiophenes
;
Reaction mechanisms
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Tetracyanoethylene combines with two molecules of thiobenzophenone in refluxing benzene to give the tetrasubstituted 1,2-dithiin 8 (21-29%) besides the corresponding thiophene derivative 9 (40-52%). The X-ray analysis of the ruby-red 8 reveals a half-chair conformation with a torsion angle of 58.9° at the disulfide bond. The thermal desulfurization 8 → 9 (benzonitrile, 100°C) proceeds with t1/2 = 26.7 h, whereas the sulfur loss induced by triethyl phosphite is a billion times faster. The mechanisms of the formation of 8 and its sulfur extrusion are discussed in the light or recent literature.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970808
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