Bromodimethylsulfonium bromide

Khan AT, Parvin T, Choudhury LH (2008) Effects of Substituents in the beta-Position of 1,3-dicarbonyl compounds in bromodimethylsulfonium bromide-catalyzed multicomponent reactions a facile access to functionalized piperidines. J Org Chem 73 8398-8402... 

UEpoxidcs can be converted to a-halo ketones by treatment with bromodimethylsulfonium bromide Olah Vankar Arvanaghi Tetrahedron Lett. 1979, 3653. 

Bromo-l-chloro-l-alkenes, 276, 277 a-Bromocyclohexanone, 73 Bromodimethylsulfonium bromide, 66-67 3/3-Biomo-8-epicaparrapi oxide, 295 Bromo-2-ethoxycyclopiopyllithium, 67-68 5-Bromo-2-furylcaibinols, 398 Bromohydrins, 70-71... 

A recent review on the uses of bromodimethylsulfonium bromide ([Mc2S Br]Br, BDMS) in organic synthesis opened a subject of BDMS application for the one-pot synthesis of a-haloacrylates from stabilized phosphorus ylides and aldehydes in high Z/E ratios, together with other reactions.The procedure is suggested to involve a rapid in situ formation of mixed phosphonium-sulfonium ylides followed by conversion into a-halo-phosphonium yUde, e.g. Ph3P=C(Br)COOR, and subsequent Wittig reaction. 

Bromodimethylsulfonium bromide (BDMS)-catalyzed synthesis of substituted pyrroles through a one-pot four-component reaction. 

Other catalysts, such as ZrCl [16] and cellulose sulfuric acid (CSA) [17], have been also reported to activate the Ugi-3CR. In this context, Khan et al. have described the nse of bromodimethylsulfonium bromide (9) (BDMS) as catalyst for the synthesis of a-amino amidines 10 by the reaction of aromatic aldehydes, aromatic amines, and isocyanides (Scheme 7.4) [18]. 

Besides Bi(N03)3.5H20 and CAN, few more catalysts such as bromodimethylsulfonium bromide (BDMS) [1], tetrabutylammonium tribromide (TBATB) [2], molecular iodine (I2) [3], InCl3 [4], NiClj.bHjO [5], zinc hydrogen sulfate [Zn(HS04)2l [6] and LaCb.THjO [7] have also been reported to accomplish the synthesis of functionalized tetrahydropyridines using eth-anol/methanol or acetonitrile medium at room temperature. 

Type of reaction C-S bond formation Reaction conditions Acetonitrile, room temperature Synthetic strategy Thiocyanation of aromatic compounds Cataiyst Bromodimethylsulfonium bromide (BDMS)... 

Keywords Aromatic substrates, ammonium thiocyanate, bromodimethylsulfonium bromide (BDMS), acetonitrile, room temperature, thiocyanation, aryl thiocyanate... 

Bhalerao, D. S., and Akamanchi, K. G. (2007). Efficirait and novel method for thiocyanation of aromatic and heteroaromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate. Synlett, 2952-2956. 

Bromodimethylsulfonium bromide (BUMS) can be used to form a-bromoesters from /5-ketoesters (Eq. 6.52) [82]. The same reagent serves to brominate 1,3-diketones in the a position (Eq. 6.53). 

Scheme 17.40 Bromodimethylsulfonium bromide catalysed Beckmaim rearrangement of oximes.

Bromodimethylsulfonium bromide (BDMS) in combination with ZnCl2 has exhibited catalytic activity in the Beckmann rearrangement (Scheme 17.40). 

Bromodimethylsulfonium bromide has been reported to effect a Lessen rearrangement of hydroxamic acids to the corresponding isocyanates, which can be trapped in situ with various amines (Scheme 172). ... 

---