- SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1
-
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.
- 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)
-
- Enantioselective Pd-catalyzed hydrogenation of enesulfonamides
-
Asymmetric hydrogenation of cyclic enesulfonamides affords chiral cyclic sulfonamides using Pd(OCOCF3)2/diphosphine complexes as catalysts with up to 98% ee.
- Yu, Chang-Bin,Gao, Kao,Wang, Duo-Sheng,Shi, Lei,Zhou, Yong-Gui
-
supporting information; experimental part
p. 5052 - 5054
(2011/06/10)
-
- 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)
-
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
- Brigas,Goncalves,Johnstone
-
p. 251 - 253
(2007/10/03)
-
- Sulfur Oxidation Mediated by Imine Derivatives
-
A number of oxime and benzothiazoline derivatives have been prepared and examined as mediators of sulfur oxidation by hydrogen peroxide as oxidant in the presence of base.In all cases, sulfoxidation was observed in the presence of the mediators, whereas negligible reaction occured in the absence of mediators.Carbodiimides were also examined as mediators; they proved to be highly reactive, providing predominant oxidation directly to sulfone.
- Page, Philip C. Bulman,Bethell, Donald,Stocks, Paul A.,Heer, Jag P.,Graham, Andrew E.,et al.
-
p. 1355 - 1358
(2007/10/03)
-
- Metal-assisted reactions. Part 26.1 Catalytic reactivity and ether bond lengths in aryloxytetrazoles and aryloxypseudosaccharins
-
X-Ray structure determinations on a variety of aryloxytetrazoles 1 and aryloxypseudosaccharins 4 have shown that the central C-O-C ether linkage is remarkable in having one very long C-O bond and one very short one. The central C-O-C bond angle is close t
- Alves, Jose A. C.,Barkley, James V.,Brigas, Amadeu F.,Johnstone, Robert A. W.
-
p. 669 - 677
(2007/10/03)
-
- Substituted 2,3-dihydro-1,2,4-triazolo [4,3-b][1,2]benzisothiazol-3-amine, 5,5, dioxides
-
2,3-Dihydro-1,2,4-triazolo[4,3-b][1,2]benzisothiazol-3-amine, 5,5-dioxides having the formula STR1 and salts thereof are new compounds which are useful as anti-inflammatory agents.
- -
-
-