4282-33-1Relevant articles and documents
Site selectivity of the diels-alder reactions of 3-[1-(tert-butyldimethylsilyloxy)vin-1-yl]furan and 3-(propen-2-yl)furan. Synthesis of 4-substituted benzofurans
Benítez, Aida,Herrera, F. Ruth,Romero, Margarita,Talamás, Francisco X.,Muchowski, Joseph M.
, p. 1487 - 1489 (2007/10/03)
The Diels-Alder reaction of 3-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.
Synthesis and Reactions of 3,4-Bis(trimethylsilyl)furan and 2-Methyl-3,4-bis(trimethylsilyl)furan
Ho, Mei Sing,Wong, Henry N. C.
, p. 1238 - 1240 (2007/10/02)
3,4-Bis(trimethylsilyl)furan (2) and 2-methyl-3,4-bis(trimethylsilyl)furan (3) have been synthesised and found to undergo a Diels-Alder reaction as well as a regiospecific Friedel-Crafts acylation (regioselective desilylation), regiospecific deuteriodesilylation.
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.