37902-49-1Relevant articles and documents
?-Facial Diastereoselectivity in Diels-Alder Reactions of 2,5-Dimethylthiophene Oxide
Naperstkow, Arvin M.,Macaulay, John B.,Newlands, Michael J.,Fallis, Alex G.
, p. 5077 - 5080 (1989)
A series of cycloadditions with 2,5-dimethylthiophene oxide (2), generated in situ by peracid oxidation of 2,5-dimethylthiophene (1), are described.In all cases the syn adduct (with respect to the sulfoxide oxygen) is formed exclusively.
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.
Arene synthesis by extrusion reaction X. Synthesis of arenes by deoxygenation of endoxides with cyclopentadienyltitanium trichloride/lithium aluminum hydride and dicyclopentadienyltitanium dichloride/lithium aluminum hydride
Wong, Chi Hung,Hung, Chi Wai,Wong, Henry N. C.
, p. 9 - 14 (2007/10/02)
The two homogeneous systems, cyclopentadienyltitanium trichloride/lithium aluminum hydride and dicyclopentadienyltitanium dichloride/lithium aluminum hydride have been utilized to deoxygenate 1,4-endoxides in tetrahydrofuran.The results show that they can provide corresponding arenes in fair yields.
