Benzyl ethyl sulfone

TABLE 12. Relative rates of H/D exchange of the diastereotopic protons in benzyl methyl sulfoxide and relative amount of 40 and 41 formed upon quenching of a-lithiobenzyl ethyl sulfone with D20 (after Reference 56)... 

Preparation of Polystyrene-g-(Benzyl-Ethyl-Sulfonaniide)Octafluoro-Butane-l-Sulfonic acid... 

The kinetics of decomposition of dimethylsulfone (DMS) benzyl methyl sulfone (BMS) and allyl methyl sulfone (AMS) were sudied by the toluene carrier flow technique over the temperature ranges 510-640 °C, 390-480 °C and 360-460 °C, respectively . The products of all three reactions contained CH4, SO2, ethyl-... 

When tosyl azide is treated with ethyl (benzylsulfonyl)pyruvate 186 in the presence of triethylamine89, benzyl diazomethyl sulfone (187) is obtained in 64% yield via the intermediate (equation 98). The latter serves as a useful reagent for the preparation of benzyl tosyloxymethyl sulfone (189) from p-toluenesulfonic acid. 

Benzyl ethyl sulfide allowed to react with 1,4-diazabicyclo [2.2.2] octane bromine complex in aq. 70%-acetic acid benzyl ethyl sulfoxide. Y 95%. — The reaction is very rapid. The products are completely free from sulfones. Neither cleavage of aliphatic G-S-bonds, which may occur when N-bromosuccinimide is used, nor ar. bromination, when bromine is used, has been observed. F. e., also O-labeled sulfoxides with 0-enriched water, and use of bromine complexes with pyridine and quinoline, s. S. Oae et al.. Bull. Ghem. Soc. Japan 39, 364 (1966). 

The procedure described is essentially that of Ballard and Dehn.1 Stilbene has also been prepared by reduction of desoxy-benzoin,20 benzaldehyde,23 and benzil 2o-2c by dehydrogenation of ethyl benzene,30 toluene,30- 33- 3, and bibenzyl 33-3alkaline reduction of phenylnitromethane,40 phenylnitroacetonitrile,40 and desoxybenzoin 43 by distillation of benzyl sulfone,50 benzyl sulfide,60-63 calcium cinnamate,5 cinnamic acid,5d phenyl cinna-mate,6e-6/ and diphenyl fumarate ie by dehydrohalogenation of a,a -dichlorobibenzyl60 and benzyl chloride 63 by dehalogenation of a,a,c/,a -tetrachlorobibenzyl70 and benzal chloride 73 by the coupling of cinnamic acid and phenyldiazonium chloride 8 by de-... 

Scheme 8 Synthesis of 4-benzyl-6-ethyl-5-methyl-l,3-oxazinan-2-one 26 via the TV-alkoxy-carbonylamino sulfone pathway...

Optimization of the previously reported Mannich-type reaction of trimethyl (pent-2-en-3-yloxy)silane with the sulfone Is derived from phenyl acetaldehyde (Table 5, entry 11) led to the corresponding (3-amino ketone in a good yield with moderate diastereoselectivity (2 mol% Bi(0Tf)3-4H20, yield = 84%, 24v/24v syn/anti = 72 28) (Scheme 8). Reduction of the major diastereoisomer 24v with lithium tri-ferf-butoxyaluminohydride afforded 25 as the only one diastereoisomer. Further cyclization of the latter with NaH afforded 4-benzyl-6-ethyl-5-methyl-l,3-oxazinan-2-one 26. The relative configuration of the six-membered carbamate was established as cis-cis by NMR analysis. 

Cesium fluoride has been used to displace halogens, sulfonate groups and nitro groups among others, with fluorine. 1-Bromooctane (1), ethyl bromoacetate (2), benzyl bromide (3) and octyl tosylate (4) have been converted to the respective fluorides 5-7 by treatment with cesium fluoride in the presence of 10% tetraalkylammonium salt (Bu4NBr or Aliquat 336) in the absence of solvent.166... 

Aromatic esters and sulfonates (benzyl acetate, ethyl p-toluene-sulfonate) accumulator column 6 46-87 69 7-17 12 d... 

Neutral alumina (1.5 g) was thoroughly mixed with iodobenzene diacetate (532 mg, 1.65 mmol) and benzyl phenyl sulfide Id (300 mg, 1.5 mmol) using a pestle and mortar. The adsorbed material was placed in an alumina bath inside the microwave oven and irradiated at 50% power for two successive intervals of 45 s each (with time interval of 3-4 min bath temperature rose to 80-85 °C). The progress of the reaction was monitored by TLC (hexane-ethyl acetate, 7 3, v/v). When the reaction was complete the whole material was directly charged onto a silica gel column which provided iodobenzene on elusion with hexane (100 mL). The fractions eluted by chloroform-hexane (1 1 v/v) provided sulfone (<7% by... 

Of an extensive series of 1-benzyl-4-[2-(/V -benzoylamino)ethyl]piperidme derivatives, designed and evaluated as inhibitors of acetylcholinesterase, the sulfone derivative (273) was the most potent (342). 

Use of thiirane 1,1-dioxide affords a useful synthesis of ethanesulfinates with the following functions in the 2-position thiol, disulfide, trisulfide, thiosulfate, thiosulfonate, and phos-phorthioate. Reaction of episulfone (83) with sodium p-toluenethiolate gives the sulfinate (84), which can be converted to the sulfone (85) (Scheme 35). Similarly, (83) is converted to the benzyl counterpart (86), which is desired for possible debenzylation to the thiol since the salt (86) is difficult to purify, it is converted to the ethyl ester (87) <86JOC5235>. 

This zinc-promoted reaction has been used with a variety of carbonyl compounds. Thus, the Luche conditions were applied in a synthesis of (-1-)-muscarine using an aldehyde derived from ethyl lactate [109]. Allyl halide condensation onto a-ketoamides of proline benzyl ester gave good diastereoselec-tivity when performed in the presence of zinc dust and pyridinium p-toluene-sulfonate in a water/THF mixture. In this way, a-hydroxy ketones were obtained with good enantioselectivity after removal of the chiral auxiliary [110]. Reactions of allyl bromide under the Luche conditions with y-aldo esters afforded y-hydroxy esters, which were converted in a one-pot reaction to y-allyl-y-butyro-lactones (Scheme 22) [111]. 

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