- A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation
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With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).
- Kotturi, Santosh R.,Tan, Jason S.,Lear, Martin J.
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supporting information; experimental part
p. 5267 - 5269
(2009/12/24)
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- Novel reactions of S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate
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S,S'-Bis(1-phenyl-1H-5-yl) dithiocarbonate (1) was synthesized in good yield from 1-phenyl-5-mercapto-5H-tetrazole (2) and trichloromethyl chloroformate (TCF).The structure of 1 was confirmed by using X-ray crystal analysis.The reagent (1) could be applied to the formation of amides, Friedel-Crafts type reactions, isothiocyanate syntheses, and carbonyl group insertion reactions.Keywords - S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate; X-ray crystal analysis; amide; isothiocyanate; Friedel-Crafts reaction; carbonyl group insertion reaction.
- Takeda, Kazuyoshi,Tsuboyama, Kanoko,Takayanagi, Hiroaki,Shirokami, Rie,Takeura, Masumi,Ogura, Haruo
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p. 2334 - 2337
(2007/10/02)
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- S,S'-Bis(1-phenyl-1H-tetrazol-5-yl) Dithiocarbonate: A New Esterification Reagent
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S,S'-Bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate is a useful reagent for the esterification of carboxylic acids with alcohols, including lactonization.The reagent is conveniently prepared in good yield from 1-phenyl-5-thioxo-4,5-dihydro-1H-tetrazole and trichloromethyl chloroformate (trichloromethyl carbonochloridate) in ethyl acetate in the presence of triethylamine.Its structure was confirmed by (13)C-NMR spectrometry and single-crystal X-ray analysis.
- Takeda, Kazuyoshi,Tsuboyama, Kanoko,Takayanagi, Hiroaki,Ogura, Haruo
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p. 560 - 562
(2007/10/02)
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