Phenylsulfonyl chloride

Unlike quinoline A -oxide, which yields a mixture of quinolin-2(l//)-one and 4-(4-quinolyl)quinolin-2(l//)-one, 7-methoxy-4-phenylquinoline A -oxide (47) with phenylsulfonyl chloride and dimcthylsulfoxonium metliylide affords the l//-l-benzazepine 48 (a rare example of an 7V-unsubstituted l//-l-benzazepine), together with small amounts of the dimeric 1//-1-benzazepine 49 and 2,2-bis(7-methoxy-4-pheny]-2-quinolyl) (8% mp 276 C).166... 

The reaction of diethyl alkylphosphonates with phenylsulfonyl chloride in the presence of n-BuLi (2 eq) in THF at low temperature followed by the addition of carbonyl compounds produces diethyl l-alkyl-l,2-epoxyalkylphosphonates in 30-80% yields, whereas under the same conditions, diethyl benzylphosphonates give comparable quantities of 1-phenyl-1-chloroalkenes (35-55%, Scheme 3.28). Similarly, p-iminophosphonate carbanions, obtained from diethyl 1-lithiomethylphosphonate and nitriles, react with phenylsulfonyl chloride in THF at -78°C. Hydrolysis (3 M H2SO4) of the resulting a-chloro-p-enaminophosphonates produces diethyl a-chloro-P-ketoalkylphosphonates in satisfactory yields (53-67%). ... 

Diethyl methylphosphonate reacts with phenylsulfonyl chloride (2 eq) in the presence of n-BuLi (3 eq) to produce diethyl 1-lithio-1,1-dichloromethylphosphonate, which can be quenched in quantitative yield or reacted directly with a large variety of carbonyl compounds (Homer-Wadsworth-Eimnons reaction), thus providing a useful one-pot process for the synthesis of dichloroalkenes. ... 

Benzenosulfochloride Benzeno-sulphochloride Benzolsulfochloride BRN 0606926 BSarefine D EINECS 202-636-6 HSDB 6004 NSC 2864 Phenylsulfonyl chloride RCRA waste number U020 UN2225. 

Oxetane-2-ones are also y lactones [4]. They are prepared by cyclodehydration of y hydroxy-carboxylic acids with phenylsulfonyl chloride in pyridine ... 

Kondo T, Abe H, Goto T (1988) Synthetic studies on gangliosides. 9. Efficient synthesis of 2a-glycoside of V-acetylneuraminic acid via phenylsulfonyl chloride adduct of 2-deoxy-2,3-dehydro-V-acetybieuraminic acid methyl ester tetra-O-acetate. Chem Lett 1988 1657—1660... 

FIGURE 10.1 (a) NMR spectra of 4-[9-(triethylsilyloxy)nonyloxy]phenylsulfonyl chloride in solution (up), (b) SR-MAS NMR spectra of polymer-supported 12 (down). 

Fluorescein (149) reacts with phenylsulfonyl chloride in DMF to yield the chloro compound (150). The proposed pathway involves initial conversion of the phenolic hydroxyl group to its phenylsulfonate, and then displacement of the sulfonate group by the chloride ion liberated in the first step. The latter step presumably involves acid-catalysed addition of chloride ion at the site of sulfonate attachment to give the gm-substituted compound (151), which upon rearomatization of ring A expels benzene sulfonate ion to give the chloro compound (150). 

Having established an eflflcient catalytic system for the nickel catalyzed Heck reaction, a more in-depth study of the mechanistic details was desired. In order to investigate the role of the leaving group, aryl sulfonates with different electronic properties were prepared from 2-naphthol and various phenylsulfonyl chloride derivatives, using the same procedures as described in Chap. 5 (Table 6.3). Relying on the optimized reaction conditions, the coupling between 2-naphthyl benzene-sulfonate and n-butyl vinyl ether resulted in a 68 % conversion (entry 1). Mixtures of... 

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