4247-57-8Relevant articles and documents
Trapping Reactions of Sulfenes Generated from Sulfonic Acid Derivatives and Bases, 2. Cycloadditions of 1,2,3,4,5-Pentamethylcyclopentadiene and 1,3-Diphenylbenzofuran with Sulfenes
Opitz, Guenter,Deissler, Michael,Rieth, Karlheinz,Wegner, Ralf,Irngartinger, Hermann,Nuber, Bernhard
, p. 2151 - 2164 (2007/10/03)
Sulfenes 2a-o, generated in situ from sulfonyl chlorides and Et3N, are trapped by 1,2,3,4,5-pentamethylcyclopentadiene (6) to give cycloadducts 8a-o containing the 7-methyl group in anti position.With mesylsulfene (7), formed in situ from mesyl chloride/Et3N in MeCN solution, the cycloaddition to endo/exo-9 (X-ray analyses) is accompanied by a (2 + 2> cycloaddition to 10 (X-ray analysis). (+)-10-Camphorsulfonyl chloride/Et3N afforded only two (and no more) diastereomeric cycloadducts (endo/exo-8d).Et3N can be replaced by Me3N, N,N,N',N'-tetramethylnaphthalene-1,8-diamine or NaH, the sulfonyl chlorides to a limited extent by sulfonyl fluorides, sulfonic acid anhydrides or aryl esters.Formation of 8p from 6 and dichloromethanesulfonyl chloride requires NaH or AgNO3 or tertiary amine/AgNO3.N-(2-Methyl-1-propenyl)pyrrolidine is more reactive than 6 in trapping sulfene 2a. 6, however, is more efficient sulfene scavenger than 1,3-diphenylbenzofuran (19), which reacts with sulfene 2d by cycloaddition and SO2 extrusion to give ketone 21d in only 18percent yield. - Keywords: 1,2,3,4,5-Pentamethylcyclopentadiene; 1,3-Diphenylbenzofuran; Sulfenes; Cycloaddition