51616-67-2

Upstream product

• 98-58-8 4-bromobenzenesulfonyl chloride 
• 1195-33-1 4-bromo-benzenesulfinic acid 
• 106-96-7 propargyl bromide 

Downstream Products

• 51082-10-1 (4-bromo-benzenesulfonyl)-acetone 
• 125704-82-7 N-[2-(4-Bromo-benzenesulfonyl)-1-methyl-eth-(Z)-ylidene]-N'-phenyl-hydrazine 

Relevant academic research and scientific papers

Homolytic Displacement at Carbon. Part 3. First Example of α-Attack on the Allenyl- and Prop-2-ynyl-cobaloximes

Allenylcobaloxime reacts with substituted benzenesulphonyl chlorides in an inert atmosphere under irradiation with tungsten lamps to give good yields of allenyl sulphones.However, the same reactions carried out in Srinivasan's photoreactor using a 400 W medium-pressure mercury lamp or under thermal conditions give exclusively prop-2-ynyl sulphones, by regiospecific rearrangement, in good yields.The corresponding reactions of (3,3-disubstituted allenyl) cobaloximes afford 1,1-disubstituted prop-2-ynyl sulphones irrespective of the conditions used.Similarly, prop-2-ynyl sulphones are formed exclusively in the reactions of prop-2-ynylcobaloxime with organosulphonyl chlorides under thermal and photochemical conditions.The reactions are believed to take place through a chain mechanism in which cobaloxime(II), present adventitiously or formed by partial homolysis of the substrate cobaloxime, abstrscts a chlorine atom from the organosulphonyl chloride to give the organosulphonyl radical RSO2.Depending upon the reaction conditions and the nature of cobaloxime, RSO2 attacks the α- or the γ-carbon atom of the axial organic group of the cobaloxime, thereby displacing cobaloxime(II) and giving the observed organic product.

HYDRATION OF 1- AND 3-ARYLSULFONYL-1-PROPYNES AND ARYLSULFONYLALLENES

The reactions of isomeric 1- and 3-arylsulfonyl-1-propynes and arylsulfonylallenes with primary aromatic amines in organic solvent-water system lead to arylsulfonyl-2-propanones.Unstable addition products (enamines) are formed in the reaction and then undergo hydration and are transformed into the ketones.

HOMOLYTIC DISPLACEMENT AT CARBON: FIRST EXAMPLE OF α-ATTACK IN THE ALLENYL AND PROPARGYL COBALOXIMES

The reactions of allenyl and propalgyl cobaloximes with organosulphonyl chlorides under anaerobic and photochemical conditions form sulphones by a novel homolytic attack at the α carbon to the metal.