72181-92-1Relevant academic research and scientific papers
Cycloaddition of thiophene S-oxides to allenes, alkynes and to benzyne
Thiemann, Thies,Fujii, Hideki,Ohira, Daisuke,Arima, Kazuya,Li, Yuanqiang,Mataka, Shuntaro
, p. 1377 - 1384 (2007/10/03)
Thiophenes have been treated with alkynes in the presence of m-chloroperoxybenzoic acid to give substituted arenes as cycloadducts. Alternatively, thiophene S-oxides have been prepared by oxidation from thiophenes and have been subjected to cycloaddition with alkynes in a subsequent step. The outcome of the reaction is dependent on the steric demand of the thiophene S-oxide. Some thiophene S-oxides can be reacted at temperatures as high as 140°C without decomposition. Thiophenes as deoxygenated products are the main by-products. Reactions of thiophene S-oxides with allenes give in part thiabicyclo[2.2.1]heptene S-oxides of type 12a and 13 along with aromatized products. Thiophene S-oxides also cycloadd to benzyne.
