3-benzyl-2-methyl- -trifluoromethanesulfonate

DIKETONES l-Benzyl-4-(2-hydioxy-ethyl)-5-methyl-l, 3-thiazolium chloride. Copper(II) trifluoromethanesulfonate. 

The seven-membered phostone 252 was synthesized by the reaction of methyl 2,3-di-0-benzyl-4,6-0-benzyl-idene-a((3)-D-glucopyranoside 251 with triethyl phosphate and trimethylsilyl trifluoromethanesulfonate. Protecting the acetal group of 251 interacted with triethyl phosphite and opened to give 252, which can be further selectively hydrolyzed or deprotected to give 253 or 254 <2003TL8797>. 

Abbreviations Ac acetyl AIBN azobisisobutyronitrile All allyl Bn benzyl Bz benzoyl ClAc chloroacetyl DAST diethylaminosulfur trifluoride DBU l,8-diazabicyclo[5.4.0]-undec-7-ene DDQ 2,3-dichloro-5,6-dicyano-/)-benzoquinone DMDO dimethyldioxirane DMTST dimethyl(methylthio)sulfonium trifluoromethanesulfonate Fmoc 9-fluorenyl-methoxycarbonyl HDTC hydrazine dithiocarboxylate IDCP iodonium di-collidine perchlorate Lev levulinoyl MBz 4-methylbenzoyl Me methyl MEK methyl ethyl ketone MP 4-methoxyphenyl NBS iV-bromosuccinimide NIS A-iodosuccinimide Pent n-pentenyl Pfp pentafluorophenyl Ph phenyl Phth phthaloyl Piv pivaloyl PMB 4-methoxybenzyl TBAF tetrabutylammonium fluoride TBDMS tcrt-butyldimethylsilyl TBDPS tert-butyldiphenylsilyl TCA trichloroacetyl TES triethylsilyl Tf trifluoromethanesulfonyl TMS trimethylsilyl Tol 4-methylphenyl Tr trityl Troc 2,2,2-trichloroethoxycarbonyl Ts tosyl. 

Abbreviations Ac acetyl Bn benzyl Cu(OTf)2 copper triflate Et ethyl HOTf trifluoromethanesulfonic acid KHMDS potassium hexamethyldisilazane Kim potassium imidazole / Hx / Hexyl Me methyl ... 

Figure 21.7 Novel ionic liquids for CC column coating, (a) l-Benzyl-3-methylimidazolium trifluoromethanesulfonate [BzMIM][OTf]. (b) l-(4-Methoxyphenyl)-3-methylimidazolium trifluoromethanesulfonate [MeO-PhMIM][OTf], (c) Separation of polar/nonpolar mixture CHjClj (1), methyl caproate (2), octyl aldehyde (3), dodecane (4), octanol (5), tridecane (5), naphthalene (7), nitrobenzene (8), tetradecane (9), pentadecane (10), and octanoic acid (11). Conditions 80°C for 3min, 10°Cmin" to...

The Stevens rearrangement of azetidinium trifluoromethanesulfonate salts 96-98 possessing a methyl and benzyl group on the nitrogen in the... 

The combination of a secondary benzyl alcohol with Hf(OTf)4 in nitromethane was a highly effective secondary benzylation system. Secondary benzylation of carbon (aromatic compounds, olefins, an enol acetate), nitrogen (amide derivatives), and oxygen (alcohols) nucleophiles was carried out with a secondary benzyl alcohol and 1 mol % of Hf(OTf)4 in the presence of water. Secondary benzyl alcohols and nucleophiles bearing acid-sensitive functional groups (e.g.,icri-butyldimethylsilyloxy and acetoxy groups and methyl/benzyl esters) could be used for alkylation. Hf(OTf)4 was the most active catalyst for this alkylation, and trifluoromethanesulfonic acid (triflic acid, HOTf) also proved to be a good catalyst. In such cases, the catal)fiic activity of metal triflates and HOTf increased in the order La(OTf)3 [Pg.346]

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