393085-11-5Relevant academic research and scientific papers
Synthesis and thermal transformation of stable monocyclic λ4-thiabenzenes
Shimizu,Kudo,Kataoka,Hori
, p. 2269 - 2276 (2007/10/03)
The stable monocyclic λ4-thiabenzenes 6a-e, which are stabilized with electron-withdrawing substituents such as benzoyl, cyano and alkoxycarbonyl groups, are synthesized in high yields by proton abstraction from the corresponding thiopyranium salts 5a-e with triethylamine in ethanol. The ylidic properties of the λ4-thiabenzenes are established based on spectral and chemical evidence. Thermal decomposition of the λ4-thiabenzenes affords alkyl-rearranged products 7,8, and 9, thienofuran derivatives 10 (from benzoyl-substituted λ4-thiabenzenes), and thiophene derivatives 11. A plausible mechanism for the formation of those products is also discussed.
