57892-93-0Relevant academic research and scientific papers
Factors Affecting the Rates of Thermal Decomposition of Azidothiophenes
Dyall, Leonard K.,Suffolk, Peter M.,Dehaen, Wim,L'abbe, Gerrit
, p. 2115 - 2119 (2007/10/02)
The thermolysis rate of 4-methoxy-1-azidobenzene reveals that the methoxy group increases the rate much less than the endocyclic sulfur does in 3-azidothiophene.With 3-azidothiophene, the neighbouring groups 2-acetyl and 2-nitro enhanced the rate in decalin solution only 5- and 17-fold, respectively, whereas in azidobenzene the corresponding enhancements are 413 and 1060.It is argued that the preferred electron distribution in the transition state for decomposition of 3-azidothiophene is not consistent with that required for effective neighbouring group participation. 2-Cyano and 2-methoxycarbonyl substituents, which are not known as effective neighbouring groups in thermal decompositions of azides, have very little effect on the rate for 3-azidothiophene.
