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Episulfidation of Strained Cycloalkenes in the Thermolysis of 5-Aryloxy-1,2,3,4-thiatriazoles

✍ Scribed by Waldemar Adam; Rainer M. Bargon

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
240 KB
Volume
2001
Category
Article
ISSN
1434-193X

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✦ Synopsis

The thermolysis of 5-aryloxythiatriazoles 1 in the presence of norbornene (2a) and trans-cyclooctene (trans-2b) affords the corresponding thiiranes 3a and trans-3b in moderate yields. First-order kinetics are observed, suggesting that a sulfur in- [a]

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The mechanism of the rearrangement of 4-alkyltriazoles to the corresponding 1-alkyltriazoles on thermolysis at 330 °C is shown to involve initial formation of an intermediate 1,4dialkyltriazolium triazolate salt. The triazolate ion subsequently attacks at the alkyl group bearing 1-and 4-positions of