Trimethylsilyl methanesulfonate

Wang, M. W., Chen, Y. J., Wang, D. Catalytic aiiyiation of aldehydes with allyltrimethylsilane using in situ-generated trimethylsilyl methanesulfonate (TMSOMs) as a catalyst. Synlett 2000, 385-387. 

Completion of the total synthesis was easily accomplished in three steps (Scheme 19.36). Treatment of cycloadduct 158 with excess trimethylsilyl methanesulfonate and triethyl-amine resulted in the double elimination of the oxygen bridge to afford tropanone 159 in 62% yield. Removal of the... 

Trimethylsilyl trifluoromethanesulfonate Methanesulfonic acid, trifluoro-, trimethyIsilyI ester (8,9) (27607-77-8)... 

Bicyclo[2.2.1]hepta-2,5-diene-l,4-bis(diphenylphosphino)butanerhodium trifluoromethanesulfonate Rhodiura(l+), [(2,3,5,6- )-bicyclo[2.2.1]hepta-2,5-diene][l, 4-butanediylbi s[diphenyl phosphine]- ,P ]-, tri f1uoromethanesulfonate Bicyclo[2.2.l]hepta-2,5-diene-2,4-pentanedionatorhodiurn Rhodium, (2,5-norbornadiene) (2,4-pentanedionato)- (8) Rhodium, [(2,3,5,6- )-bicyclo[2.2.l]hepta-2,5-diene] (2,4-pentanedionato-0,0 )- (9) (32354-50-0) Trimethylsilyl trifluoromethanesulfonate Methanesulfonic acid, trifluoro-, trimethylsilyl ester (8,9) (27607-77-8)... 

Cyclizations can also be carried out with an esterified oligomer of phosphoric acid called polyphosphate ester. This material is soluble in chloroform.49 (See entries 11 and 12 in Scheme 11.4.) Another reagent of this type is trimethylsilyl polyphosphate.50 Neat methanesulfonic acid is also an effective reagent for intramolecular Friedel-Crafts acylation.51 (See entry 13 in Scheme 11.4.)... 

This method is especially useful for the conversion of ketones to ketals, since the direct reaction of a ketone with an alcohol often gives poor results. In another method, the substrate is treated with an alkoxysilane ROSiMe3 in the presence of trimethylsilyl trifluoro-methanesulfonate.91... 

By an interesting reaction involving trimethylsilyl chlorosulfonate and hexamethyldisilane, two methanesulfonates containing the silicon-silicon bond have recently been prepared (13). 

Synthetically useful phosphorane-derived phenyliodonium triflates have been synthesized from the highly electrophilic pyridinium complex 20 <2002TL2359>. Similarly, benziodoxole 21 reacts with trimethylsilyl trifluoro-methanesulfonate (TMSOTf) and pyridine to form a precipitate of complex 22 (Equation 6) <2002TL5735>. The first example of a pentavalent iodine complex with a chelating polydentate nitrogen ligand 24 was obtained from diacetate 23 under similar conditions (Equation 7) <2002TL5735>. 

Trimethylsilylmethylmagnesium chloride Magnesium, [chk>ro[(trimethylsilyl)-methyl)- (13170-43-9), 69, 89 3-Trimethylsilyl-2-propyn-1-ol, 66,1, 3 3-Trimethylsilyl-2-propyn-1-yl methanesulfonate, 66, 2... 

Protodesilylation of allyl- or aryl-substituted trialkylsilanes with an acid partner is a cleaner method, producing propene or an aromatic hydrocarbon as a volatile inert byproduct. Although some methods of isolation have been reported, they can usually be prepared in situ in aprotic media and employed without further purification. Methods of preparation of representative organosilicon Lewis acids, la, trimethylsilyl bis(trifluoro-methanesulfone)imide (7) [9], trimethylsilyl perchlorate (6a) [10], iodotrimethylsilane, and trimethylsilyl tetrakis(trifluoromethanesulfonyl)borate [11] are described below. In principle, these analogs are also accessible in a similar manner (Table 1) [2d]. 

It has been observed that the reaction of methyl 2,3-di-0-benzyl-4,6-benzyli-dene-a(p)-D-glucopyranoside with triethyl phosphite and trimethylsilyl triflu-oro-methanesulfonate leads unexpectively to seven-membered phostone (394). Removal of protecting groups from the phostone is also reported (Figure 68). The simple transformation of carbohydrate-derived y-hydroxyphosphonic acids (395) into the corresponding phostones (396) using standard acylation conditions has been described (Scheme 97). 

Its derivative, bis(trimethylsilyl) peroxide, effects the Baeyer-VilUger reaction in aprotic solvents in the presence of trimethylsilyl trifluoro-methanesulfonate [237] (see equation 388). 

Then preparation of the oxazoline 7b has been achieved by treatment of compound 7a with trimethylsilyl trifluoro-methanesulfonate (TMSOTf) in ethyl acetate at 52°C. 

Norsedamine (177) was reported to competitively inhibit pea diamine oxidase (Ki=0.03 mM) [445]. Racemic 177, as well as 171, was synthesized using the trimethylsilyl trifluoro-methanesulfonate-catalyzed addition of 1-trimethylsilyloxy-l-phenylene to A-r-butoxycarbonyl-2-ethoxypyridine as a key step [451]. 

MMTS MsOH NBS NHMDS NMP NMR PPb Ph Pr PTC rt TBDMS Tf THF THP TLC TMEDA TMS TMSOTf Tol TOMAC Ts TsOH UDP methyl methylthiomethyl sulfoxide (=FAMSO) methanesulfonic acid N-bromosuccinimide sodium hexamethyldisililazide /V-methyl-2-pyrrolidone nuclear magnetic resonance parts per billion phenyl propyl Phase transfer catalysis room temperature t-butyldimethylsilyl triflatc (trifluoromethanesulfonate) tetrahydrofuran 2-tetrahydro-2//-pyran-2-yl thin-layer chromatography /V./V./V /V -tetramethylethylenediamine trimethylsilyl trimethylsilyl triflate p-tolyl trioctylmethylammonium chloride tosyl p-toluenesulfonic acid ultrasonically dispersed potassium... 

The initial report of the synthesis of (trimethylsilyl)methanesulfonyl chloride100 described its ready hydrolysis to hexamethyldisiloxane and methanesulfonic acid, the reaction being complete, for example, after ten minutes in 5% aqueous sodium hydroxide at room temperature. The intermediacy of sulfene seems likely, for the alkaline cleavage at least. 

Dimethylfoimamide. Lithium diisupiupylamide. p-Toluene sulfonyUiydrazine. SILYLATION N,0-Bis(trimethyl iIyl) ulfonate. Ethyl trimethylsilylacetate. Trifluoro-methanesulfonic add trimethylsilyl ester. N-(Trimethylsilyl)imidazole. SPIROCYCLIZATION Pyriolidine. 

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