1951
DOI: 10.1021/jo01144a013
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The Preparation of Alkanesulfonyl Halides

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Cited by 35 publications
(16 citation statements)
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“…The partially protected ribonucleosides 1-10 were then sulfonated in pyridine by 2-(4-nitrophenyl)ethanesulfonyl chloride [38] which was synthesized from 2-(4-nitropheny1)ethyl chloride [39] with sodium thiosulfate and subsequent oxidation by Cl,. The yield of the 2'- matographic isolation on silica gel, in the range of 70-90%, except for the 5,6-dihydrouridine derivative 35 which is a quite labile compound and could only be obtained in 33 ?G yield.…”
Section: Ethoxycarbonyl]-o6-[2-(4-nitropheny1)ethyl] Derivatives Aftementioning
confidence: 99%
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“…The partially protected ribonucleosides 1-10 were then sulfonated in pyridine by 2-(4-nitrophenyl)ethanesulfonyl chloride [38] which was synthesized from 2-(4-nitropheny1)ethyl chloride [39] with sodium thiosulfate and subsequent oxidation by Cl,. The yield of the 2'- matographic isolation on silica gel, in the range of 70-90%, except for the 5,6-dihydrouridine derivative 35 which is a quite labile compound and could only be obtained in 33 ?G yield.…”
Section: Ethoxycarbonyl]-o6-[2-(4-nitropheny1)ethyl] Derivatives Aftementioning
confidence: 99%
“…treated with 25% NH,/H,O, kept at 8" for 20 h, and evaporated, and the residue co-evaporated with toluene/MeOH I : I . The resulting solid was crystallized from OH-C(2')); 5.20 (d,); 4.98 (t, OH-C(5')); 4.77 (t. 2 H, OCH,CH, (npeoc)); 4.60 (m, H-C(2')); 4.38 ( t , 2 H, OCH,CH, (npe)); 4.18 (m, H-C(3')); 3.92 (m, H-C (4) 2-(4-Nitrophenyl)ethanesulfonyl Chloride (Npes-C1) [38]. To a soln.…”
Section: N2-/2-(4-nitrophenyl~e~lio~yrarbon)~l]-06-(2-(cnitrophenyl)mentioning
confidence: 99%
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“…Amongst these methods, the more important involve the aqueous chlorination of disulfides and thiols [8]. Different sulfur compounds have also been converted to alkanesulfonyl chlorides, e.g., thiols [8], sulfides [9], thiocyanates [10], isothiouronium salts [11], S,S-dialkyl dithiocarbonates [12], thiol esters [8], thiosulfonates [8], sulfinyl chlorides [13], and sulfinic acids [14]. However, the disadvantages of the most of these methods are the preparation of starting materials, or unsatisfactory reaction yields or the production of side products.…”
Section: Introductionmentioning
confidence: 99%
“…A soh. of 1.0 g (1.48 mmol) of N6-benzoyl-5'-O-(dimethoxytrity1)adenosine (1) [lo] in dry CHCI, (6 ml) was cooled to -6", and then 0.062 g (0.62 mmol) of Et,N and 0.55 g (2.24 mmol) of 2-(4-nitrophenyl)ethanesulfonyl chloride [21] in CHCI, (2 ml) were added dropwise. After 45 min, the mixture was allowed to warm up to r.t., diluted with CHCI, (100 ml), washed with H,O (2 x 25 ml), dried (Na2S04), and evaporated.…”
mentioning
confidence: 99%