34774-84-0Relevant academic research and scientific papers
Benzo[c]isothiazole 2-Oxides: Three-Dimensional Heterocycles with Cross-Coupling and Functionalization Potential
Lamers, Philip,Buglioni, Laura,Koschmieder, Steffen,Chatain, Nicolas,Bolm, Carsten
supporting information, p. 3649 - 3653 (2016/11/25)
A robust method for the synthesis of benzo[c]isothiazole 2-oxides has been developed providing a range of functionalized derivatives starting from anilines and DMSO. The reaction sequence can be performed on a gram scale and leads to products that can easily be modified by standard cross-coupling reactions. (Figure presented.).
Novel generation of phenylnitrenium ions from S,S-dialkylanilinosulfonium salts in trifluoroacetic acid and formation of anilines by a new intramolecular hydride-shift to the phenylnitrenium ions
Takeuchi, Hiroshi,Taniguchi, Tomohito,Masuzawa, Mamoru,Isoda, Kazuya
, p. 1743 - 1746 (2007/10/03)
Reactions of S,S-dialkylanilinosulfonium salts in trifluoroacetic acid give anilines, trifluoroacetanilides and dialkyl sulfoxides via novel intramolecular hydride-shift from the α-C-H of sulfide to phenylnitrenium ions (not completely free from the sulfide) interacting with both the unshared electron pair of the sulfide and the counter ion.
Formation of Sommelet-Hauser-Type Products, 2-Aminoarylmethyl Sulphides, and Nitrenium Ion Products, 2- and 4-Aminoaryl Sulphides, via an N-Arylazasulphonium Salt
Takeuchi, Hiroshi,Itou, Kazuaki,Murai, Hirotaka,Koyama, Kikuhiko
, p. 3156 - 3188 (2007/10/02)
Reactions of a salt (1) formed at -60 deg C from trifluoroacetic anhydride and dimethyl sulphoxide (DMSO) with primary and secondary arylamines gave 2-aminoarylmethyl sulphides (6), (6') and (12) by a Sommelet-Hauser rearrangement of an ylide (5) formed by loss of a methyl proton of an N-arylazasulphonium salt (3) in the absence of base.The use of ethyl methyl sulphoxide instead of DMSO afforded a similar product (19b) by loss of not the ethyl but the methyl proton.However, the use of diethyl sulphoxide merely caused loss of an ethyl group from the N-arylazasulphonium salt to yield ethanesulphenanilide (20).The reaction of (1) with N-phenyl-1-naphthylamine gave mainly aminoaryl sulphides (13) and (14) via an arylnitrenium ion from the N-arylazasulphonium salt.In fact, the reaction of dimethyl sulphide (DMS) with arylnitrenium ions formed in the acid decomposition of aryl azides gave no Sommelet-Hauser-type products but 2- and 4-aminoaryl sulphides (22), (22') and (23).We also discuss the possibility of the N-arylazasulphonium salt being formed by reaction of the arylnitrenium ion with DMS.
Thermal Reaction of Arylnitrenes with Dimethyl Sulphide, Thioanisole, and Tetrahydrothiophene
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 625 - 627 (2007/10/02)
The thermal decomposition of the aryl azides (1) into dimethyl sulphide (2), thioanisole (3), and tetrahydrothiophene (4) generally affords the 2-substituted anilines (5)-(7) in practicable yields by Sommelet-Hauser rearrangement of the intermediate N-arylsulphimides (11a-c) which result from arylnitrene attack at the sulphur atom of (2)-(4).This constitutes a potential synthetic procedure.
Behavior of Benzyl Sulfoxides toward Acid Chlorides. Useful Departures from the Pummerer Reaction
Chupp, John P.,Balthazor, Terry M.,Miller, Michael J.,Pozzo, Mark J.
, p. 4711 - 4716 (2007/10/02)
The present study extends the reaction of certain electrophilic reagents with electron-rich sulfides and sulfoxides beyond previously known limits.Thus, treatment of methoxy- and, more particularly, aminobenzyl sulfoxides 2 with acyl or hydrogen chlorides gives rise in high yields to the corresponding benzyl chlorides, a departure from the normally expected Pummerer reaction.It is demonstrated that ideal substrates for this reaction are o-anilines 1 derived from the well-known rearrangment of aromatic sulfilimines.Further, certain of the o-ammoniobenzyl chloride salts 4 so produced provide a basis for a novel and superior desulfurization of 1 to the corresponding o-methylaniline without resorting to Raney nickel.
N-Phehylsulphimide Formation and Rearrangement in the Thermal Reaction of Phenylnitrene with Sulphides
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 771 - 776 (2007/10/02)
Thermal reaction of phenyl azide (1) with thioanisole (2a), dimethyl sulphide (2b), and tetrahydrothiophen (2c) leads to the formation of 2-substituted anilines (3a-c) by Sommelet-Hauser rearrangement of the intermediate N-phenylsulphimides arising from phenylnitrene attack at the sulphur atom of (2a-c).Reaction with ethyl phenyl sulphide (2d) gives benzenesulphenanilide (8) and ethylene by cycloelimination of the resulting N-phenylsulphimide.Reaction with acyclic benzylic sulphides (2e-g) apparently leads only to the insertion products of phenylnitrene into benzylic C-H bond, presumably through Stevens rearrangement of the intermediate sulphimides, whereas Sommelet-Hauser rearrangement appears to compete favourably with Stevens rearrangement in the sulphimide resulting from reaction of phenylnitrene with the cyclic benzylic sulphide (2h).
Thermal Reaction of Phenylnitrene with Sulfides
Benati, Luisa,Grossi, Mario,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 763 - 765 (2007/10/02)
Thermolysis of phenyl azide in the presence of sulfides bearing α-hydrogen atoms leads to the formation of significant amounts of 2-substituted anilines, presumably by Sommelet-Hauser type rearrangement of the intermediate N-phenylsulfimides.
Herbicidal sulfonamides
-
, (2008/06/13)
This invention relates to a novel class of N-(heterocyclicaminocarbonyl)-o-alkoxymethylbenzene sulfonamide herbicides.
Process for preparing azasulfonium halide salts
-
, (2008/06/13)
Preparing azasulfonium halide salt derivatives of an aniline by reacting a halogen with a non-carbonylic dihydrocarbon sulfide, a beta-carbonylic hydrocarbon sulfide, or a β-thio ester or amide to form a halogen: sulfur compound complex and then reacting the complex with an aniline to form the azasulfonium halide salts. The azasulfonium halide salts are useful as intermediates in processes for making ortho-alkylated anilines, indoles, and 2-oxindoles which have a variety of known uses.
