110871-40-4

Upstream product

• 917-54-4 methyllithium 
• 78-84-2 isobutyraldehyde 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 75-16-1 methylmagnesium bromide 
• 842120-98-3 N-(1,2-dimethylpropylidine)-p-toluenesulfonamide 
• 563-80-4 3-methyl-butan-2-one 
• 6873-55-8 p-tolylsulfinyl amide 
• 544-01-4 isopentyl ether 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 598-74-3 2-amino-3-methylbutane 
• 917-64-6 methyl magnesium iodide 
• 5048-64-6 2,2-dimethyl-1-(toluene-4-sulfonyl)aziridine 

Relevant academic research and scientific papers

A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines

Described is a new hydrazone-based exo-directing group (DG) strategy developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. Conveniently synthesized from protected primary amines, the hydrazone DGs are shown to site-selectively promote the β-acetoxylation and tosyloxylation via five-membered exo-palladacycles. Amines with a wide scope of skeletons and functional groups are tolerated. Moreover, the hydrazone DG can be readily removed, and a one-pot C-H acetoxylation/DG removal protocol was also discovered. All about the DGs: A hydrazone-based exo-directing group (DG) strategy is developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. The hydrazone DGs can be conveniently installed and removed, and promote β-acetoxylation and tosyloxylation via a five-membered exo-palladacycle. PG=protecting group, Ts=4-toluenesulfonyl.

The mechanism of alkene elimination from protonated toluenesulphonamides generated by electrospray ionisation

The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = CnH2n+1 (n = 1-7), CnH2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = CnH2n+1 (n = 1-8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent unless energised by collision. Two general fragmentations are observed: firstly, elimination of an alkene, CnH2n, obtained by hydrogen abstraction from one of the CnH2n+1 alkyl groups on nitrogen; secondly, cleavage to form CH3C6H4SO2+. The mechanism by which an alkene is lost has been probed by studying the variation of the intensity of the [M + H - CnH2n]+ signal with the structure of the alkyl substituent(s) on nitrogen and by monitoring the competition between the loss of different alkenes from protonated unsymmetrical sulphonamides in which two different alkyl groups are attached to nitrogen. This fragmentation is favoured by branching of the alkyl group at the carbon atom directly attached to nitrogen, thus suggesting that it involves a mechanism in which the stability of the cation obtained by stretching the bond connecting the nitrogen atom to the alkyl group is critical. This interpretation also explains the competition between alkene elimination and cleavage to form CH3C6H4SO2+ (and, in some cases, cleavage to form C6H5CH2+ or [C6H5CHCH3]+).

Br?nsted acid-assisted N-alkylation of sulfonamides using ethers as the alkylation reagents

N-Alkylation of sulfonamides using cyclic ethers as alkylation reagents and Br?nsted acid as a catalyst produced pyrrolidine and piperidine derivatives in good yields. When using symmetrical and unsymmetrical ethers as alkylation reagents, mono-N-alkylation of sulfonamides took place to afford the corresponding products.

Reduction of sulfonylimines with raney nickel

Raney-Ni/EtOH reduction of different N-sulfonylimines provides a new entry for synthesizing sulfonamides in good yields under mild conditions. This protocol, which does not require additional hydrogen, constitutes a cheap, safe, and easy-to-handle alterna

Reactions with aziridines - 39. Ring opening of activated 2,2-dimethylaziridines by grignard reagents. A mechanistic study

Reaction of activated 2,2-dimethylaziridines 1 with Grignard reagents RMgHal in boiling THF can yield the products 2 of normal aziridine ring opening, the rearranged opening products 3, and the methallylamides 4 (isomers of 1 ). The product distribution depends on R, Hal, and experimental conditions, and very strongly on the nature of the activating group A. It is shown that 1 is opened (reversibly for A = sulfonyl) forming 10 through a Lewis acid assisted attack of Halθ on the tert carbon of 1 (abnormal opening by Halθ ). Evidence is presented to show that 4 as well as 3 come from this intermediate.