4482-01-3Relevant articles and documents
TRIFLUOROMETHYL THIOLATION AGENT, TRIFLUOROMETHYL THIOLATION METHOD, AND N-(SUBSTITUTED SULFONYL)-N-[(TRIFLUOROMETHYL)THIO]SUBSTITUTED SULFONAMIDE COMPOUND
-
Paragraph 0063; 0069, (2017/08/02)
PROBLEM TO BE SOLVED: To provide a new trifluoromethyl thiolation agent, a trifluoromethyl thiolation method, and an N-(substituted sulfonyl)-N-[(trifluoromethyl)thio]-substituted sulfonamide compound. SOLUTION: Provided is a trifluoromethyl thiolation agent represented by a compound represented by formula (I) or the like:(R1 and R2 respectively independently denote a halogeno group, cyano group, unsubstituted/substituted alkyl group, unsubstituted/substituted cycloalkyl group, unsubstituted/substituted alkenyl group, unsubstituted/substituted alkynyl group, unsubstituted/substituted aryl group, unsubstituted/substituted heterocyclic group, unsubstituted/substituted alkoxy group, unsubstituted/substituted aryloxy group, an unsubstituted/substituted heterocyclic oxy group or the like; R1 and R2 may coupled to form a ring). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
Reactions of arenediazonium o-benzenedisulfonimides with aliphatic triorganoindium compounds
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano,Ghigo, Giovanni
scheme or table, p. 862 - 868 (2009/04/11)
The reaction of various arenediazonium o-benzenedisulfonimides with aliphatic triorganoindium compounds is described. Surprisingly, with triethyl- or tributylindium we obtained N-ethyl- or N-butylanilines, respectively. This is the first case in which, at least formally, the reactive site of a diazonium salt is the nitrogen atom directly bonded to the aromatic ring. In contrast, with trimethylindium we obtained only formaldehyde (aryl)hydrazones. In order to explain the difference between trimethyl- and triethylindium we have proposed some reaction mechanisms, supported by detailed density functional (DFT) calculations. The possible role of diazene/hydrazone tautomerism initially assumed was discarded and therefore three mechanisms for the key step (nucleophilic addition of the trialkylindium to the N=N double bond of diazene) were studied. For the favoured mechanism there is a difference in the energy barriers of 2 kcalmol-1 between the reactions with trimethyl- and triethylindium. This difference is explained on the basis of the different C-In bond energies in the two organometallics and it is assumed to be enough to explain their different behaviour under the experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Benzylation of alcohols and phenols with N-(4-methoxybenzyl)-o- benzenedisulfonimide
Carlsen, Per H.J.
, p. 1799 - 1802 (2007/10/03)
N-(4-methoxybenzyl)-o-benzene disulfonimide was prepared from o- benzenedisulfonyl chloride and 4-methoxybenzylamine in dichloromethane. Reaction of this compound with alcohols or phenols undere basic conditions gave the corresponding 4-methoxybenzyl ethers in good yields. Primary alkylamines were converted to the corresponding alcohols by treating the benzenedisulfonimido derivative with aqueous KOH in DMF solution.