19719-98-3

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 123500-71-0 (E)-1-chloro-1,2-bis(phenylsulphonyl)ethylene 
• 97760-26-4 2,3-bis(phenylsulphonyl)bicyclo<2.2.1>hepta-2,5-diene 
• 132555-54-5 5,6-Bis-benzenesulfonyl-5-chloro-bicyclo[2.2.1]hept-2-ene 
• 132555-53-4 (Z)-1-chloro-1,2-bis(phenylsulphonyl)ethylene 
• 75-16-1 methylmagnesium bromide 
• 97760-26-4 2,3-bis(phenylsulfonyl)bicyclo[2.2.1]hepta-2,5-diene 
• 917-64-6 methyl magnesium iodide 
• 2525-41-9 1-(phenylsulfonyl)propyne 

Downstream Products

• 19719-96-1 (+/-)-exo-3-methylene-2-(phenylsulfonyl)bicyclo[2.2.1]hept-5-ene 
• 19719-96-1 (+/-)-endo-3-methylene-2-(phenylsulfonyl)bicyclo[2.2.1]hept-5-ene 
• 19719-99-4 2-Benzolsulfonyl-3-methyl-bicyclo<2.2.1>hepten-(2) 

Relevant academic research and scientific papers

Conversion of γ-substituted bicyclo[2.2.1] (Z)-vinylsulfones to the corresponding (E)-allylsulfones

The preparation of bicyclo[2.2.1] (E)-allylsulfones starting from the corresponding (Z)-vinylsulfones is described. Starting from 2,3- bis(phenylsulfonyl)norbornadiene 1, the Michael addition of organometallic reagents followed by the base catalyzed isome

(Z)-AND (E)-1-CHLORO-1,2-BIS(PHENYLSULPHONYL)ETHYLENES: SYNTHONS OF BIS(PHENYLSULPHONYL)ACETYLENE AND OF TERMINAL ACETYLENES IN CYCLOADDITION REACTIONS

The cycloaddition reaction of both isomeric 1-chloro-1,2-bis(phenylsulphonyl)ethylenes 1 leads to the expected Diels-Alder adducts with a number of dienes.The (Z)-isomer is more reactive, but the adducts are dehydrochlorinated with more difficulty and in lower yields than the adducts derived from the cycloaddition of the (E)-isomer.The dehydrochlorinated products are bis(phenylsulphonyl)alkenes which formally derive from the cycloaddition of the hitherto unknown bis(phenylsulphonyl)acetylene.These compounds undergo addition-elimination reaction with Grignard reagents; the products, desulphonylated by sodium amalgam, can be considered as the Diels-Alder adducts of terminal acetylenes.

1,2-BIS(PHENYLSULFONYL)ALKENES AS VERSATILE GROUPS IN ORGANIC SYNTHESIS: THE PREPARATION OF ALKYL- AND ARYL-SUBSTITUTED NORBORNADIENES VIA THE DIELS-ALDER CYCLOADDITION - GRIGNARD REACTION - DESULFONYLATION SEQUENCE

A synthetic methodology for the preparation of the formal Diels-Alder cycloadducts of alkyl- and aryl-substituted acetylenes which exemplifies the utility of bis(phenylsulfonyl)alkenes 1 in organic synthesis is presented.The procedure entails -cycloaddition of (e)-1,2-bis(phenylsulfonyl)-1-chloroethylene (4), grignard reaction and desulfonylation; each step occurs in high yield.