18712-15-7Relevant articles and documents
SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1
Maricich, Tom J.,Allan, Matthew J.,Kislin, Brett S.,Chen, Andrea I-T.,Meng, Fan-Chun,Bradford, Christine,Kuan, Nai-Chia,Wood, Jeremy,Aisagbonhi, Omonigho,Poste, Alethea,Wride, Dustin,Kim, Sylvia,Santos, Therese,Fimbres, Michael,Choi, Dianne,Elia, Haydi,Kaladjian, Joseph,Abou-Zahr, Ali,Mejia, Arturo
, p. 3361 - 3368 (2014/01/06)
Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4- nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate. Georg Thieme Verlag Stuttgart . New York.
A reagent for the convenient, solid-phase synthesis of N-Terminal peptide hydroxylamines for chemoselective ligations
Fukuzumi, Takeo,Bode, Jeffrey W.
supporting information; experimental part, p. 3864 - 3865 (2009/08/08)
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Electronic effects on C-O-C ether bonds in 3-aryloxy derivatives of benzisothiazole 1,1-dioxides: rapid ethanolysis of 3-(4-nitrophenoxy)-1,2-benzisothiazole 1,1-dioxide, (1), to give 3-ethoxy-1,2-benzisothiazole 1,1-dioxide, (2)
Brigas,Goncalves,Johnstone
, p. 251 - 253 (2007/10/03)
The bond lengths in the central C-O-C ether link-age of title compound (1), C13H8N2O5S, are comparable with those found in earlier work on similar compounds. However, (1) was found to undergo very easy solvolysi
