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.
MOLYBDENUM-PROMOTED REACTIONS OF 7-OXABICYCLOHEPTADIENE AND DERIVATIVES
Sun, Chia-Hsing,Chow, Tahsin J.
, p. 217 - 226 (2007/10/02)
The reactions of 2,3-bis(methoxycarbonyl)-7-oxabicycloheptadiene (1a) and related compounds 1b, 1c, and 2 with molybdenum carbonyl complexes are examined at two different temperatures.In refluxed cyclohexane, reactions of 1a-c with hexacarbonylmolybdenum produce mainly the corresponding derivatives of dimethyl phthalate (3a-c) and 3,4-bis(methoxycarbonyl)furan (4a-c), while the reaction of 2 produces naphthalene and 1-naphthol.At room temperature, reactions of 1a,b with tris(acetonitrile)tricarbonylmolybdenum yield the dimer ketones 5a,b in addition to 3a,b and 4a,b, while the reaction of 2 produces naphthalene as the only prod uct.The mechanism for the generation 3, 4, and 5 is rationalized as going through complex intermediate with structure of a molybdenum chelated by 1.