Sodium benzenesulfinate

The reacdon of ct-bromo or ct-iodorutroalkanes with sodium benzenesulfinate gives ct-n sidfones in 85-95% yields fEq. 5.73, which proceeds via Ssj l reacdon fSecdon 5.4 / ... 

The reaction of a-bromo or a-iodonitroalkanes with sodium benzenesulfinate gives a-nitro sulfones in 85-95% yields (Eq. 5.73), which proceeds via SRN1 reaction (Section 5.4).117... 

Due to the importance of this heterocycle in medicinal chemistry, solid-phase synthesis of derivatives based on this condensation reaction have been investigated. The first report in this area uses a sodium benzenesulfinate resin 247 and gives access in five steps and good overall yields to a library of imidazo[l,2- ]pyridines 248 functionalized at C-2 with an enone moiety <2002OL3935>. Later on, the preparation of libraries of compounds related to 250 or 251 from Rink amide resin 249 have been published (Scheme 68) <2003TL6265>. 

Evidence for a Michael addition of a nucleophile to alkenyl(phenyl)iodonium salts at the Cp atom has now been reported for the first time. Nucleophilic vinylic substitutions of (Z)-(/3-bromoalkenyl)iodonium tetrafiuoroborates (161) and its (Z)-(/3-chloroalkenyl) analogue with sodium benzenesulfinate in THE afforded stereoselectively (Z)-l,2-bis(benzenesulfonyl)alkene (163) with retention of configuration. Intermediate formation of (Z)-[/3-(benzenesulfonyl)alkenyl]iodonium salt (162) in these reactions was established by NMR experiments in CDCI3. The formation of (Z)-(162) involves a hitherto unobserved Michael addition of benzenesulfinate anion to the alkenyliodonium salts at the Cp atom, followed by halogen extrusion. ... 

Sodium benzenesulfinate (benzenesulfinic acid, sodium salt) was purchased from Aldrich Chemical Company, Inc. and used without further purification. 

Sulfonylation of aromatic hydrocarbons in the presence of a Lewis acid and the reaction of sodium benzenesulfinate with alkyl halides proved to be particularly easy and useful to prepare starting materials for the Julia olefination procedure (see Section 4.3.2). 

Allylic phosphorus compounds Tris(tetrabutylammonium) pyrophosphate, 338 Allylsilanes t-Butyllithium, 58 Chlorotrimethylsilane-Lithium, 81 Lithium bis(dimethylphenylsilyl)-cuprate, 161 Methyllithium, 188 Trichlorosilane-t-Amines, 322 Allylic sulfur compounds (Phenylsulfonyl)allene, 247 Sodium benzenesulfinate, 289... 

A two-phase mixture of methyl propiolate (5.0 g, 59.5 mmol), boric acid (5.5 g, 89 mmol), sodium benzenesulfinate (9.75 g, 59.5 mmol), and tetra-n-butylammonium hydrogen sulfate (3.0 g, 8.75 mmol) (Note 1) in tetrahydrofuran water (200 mL, 1 1) is stirred vigorously at room temperature for 48 hr (Note 2). The solution is acidified to pH 4 (2 N hydrochloric acid) and extracted into diethyl ether (4 x 50 mL) (Note 3). The organic layer is dried (MgSCU) and concentrated under reduced pressure to afford 13.75 g of yellow oil (Note 4) which is subjected to flash column chromatography (1.5 1 hexanes-diethyl ether) to afford initially methyl (E)-3-(benzenesulfonyl)prop-2-enoate (400 mg, 2.9%) and then the desired Z-isomer (10.89 g, 81%) as a pale yellow solid, pure by spectral study (Note 5). 

Sodium benzenesulfinate Benzenesulfinic acid, sodium salt (8,9) (873-55-2)... 

Likewise, the sulfonylhydrazones 337a-c prepared from reactions of sodium benzenesulfinate with hydrazonoyl chlorides 20a-c in ethanol at room temperature cyclized in situ to give 338a, 338b, and 339, respectively (87MI1). 

Chen Y, Lam Y, Lai YH, Solid-phase synthesis of pyrazolines and isoxazolines with sodium benzenesulfinate as a traceless linker, Org. Lett., 5 1067-69, 2003. 

This vinyl sulfone can be obtained in 70-85% yield by reaction of methyl propiolate, sodium benzenesulfinate, and boric acid (1.5 equiv.) in THF/H20 (1 1) catalyzed by Bu4NHS04. ... 

N3Na 26628-22-8) see Alfentanil Azosemide Benazepril Docetaxel Fluazacort Imiquirnod Irbesartan Midodrine Oseltamivir Paclitaxel Pemirolast Pranlukast Tazanolast Tranylcypromine Zanamivir Zidovudine sodium benzenesulfinate... 

The selenonium salts 9 and 11 were found to react with one equivalent of sodium benzenesulfinate in an alcohol giving the products shown together with their ratio in Scheme 3. It is evident from the above data that the reaction of 9 and 11 with sodium benzenesulfinate gave (Z)-alkoxyvinyl sulfone 17a and the reactions at room temperature or at 60 °C afforded (Z)-bis-(phenylsulfonyl) styrene (18) as a by-product. In contrast, the reactions of salts 9 and 11 with benze-nesulfinic acid in isopropanol afforded (Z)-()5-phenylsulfonyl)vinylselenonium salts 19 and 20 in yields of 76 and 72%, respectively (Eq. 3). Neither the sulfone 17c nor the vinylsulfone 18 was isolated from these reactions [11a]. 

It is interesting to note that the cyclic salt 12 did not react with benzenesul-finic acid however, when treated with sodium benzenesulfinate in an alcohol, it gave dibenzoselenophene 21 and Z-alkoxyvinylsulfones 17a-c in moderate yields (51-77%). When the reaction was carried out in t-butyl alcohol, bis(phenylsulfonylvinyl)ether (22) was formed in 30% yield (Eq. 4). 

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