97760-26-4

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 108-98-5 thiophenol 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 128780-28-9 2,3-dibromobicyclo[2.2.1]hepta-2,5-diene 
• 18990-07-3 2,3-dichlorobicyclo <2.2.1> hepta-2,5-diene 
• 507235-23-6 2,3-bis(phenylthio)bicyclo[2.2.1]hepta-2,5-diene 
• 134840-57-6 Bis(phenylsulphonyl)acetylene 
• 85475-95-2 bis(phenylthio)acetylene 
• 132555-54-5 5,6-Bis-benzenesulfonyl-5-chloro-bicyclo[2.2.1]hept-2-ene 
• 123500-71-0 (E)-1-chloro-1,2-bis(phenylsulphonyl)ethylene 
• 132555-53-4 (Z)-1-chloro-1,2-bis(phenylsulphonyl)ethylene 

Downstream Products

• 19719-98-3 (1S,4R)-2-Benzenesulfonyl-3-methyl-bicyclo[2.2.1]hepta-2,5-diene 
• 19719-98-3 3-methyl-2-phenylsulfonylnorbornadiene 
• 123500-74-3 1-((1R,4S)-3-Benzenesulfonyl-bicyclo[2.2.1]hepta-2,5-dien-2-yl)-naphthalene 
• 123500-73-2 (1S,4R)-2-Benzenesulfonyl-3-phenyl-bicyclo[2.2.1]hepta-2,5-diene 
• 123500-72-1 (1S,4R)-2-Benzenesulfonyl-3-propyl-bicyclo[2.2.1]hepta-2,5-diene 
• 27770-83-8 endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene 
• 74437-39-1 2-Phenylbicyclo<2.2.1>hepta-2,5-dien 
• 19719-96-1 (+/-)-endo-3-methylene-2-(phenylsulfonyl)bicyclo[2.2.1]hept-5-ene 
• 19719-96-1 (+/-)-exo-3-methylene-2-(phenylsulfonyl)bicyclo[2.2.1]hept-5-ene 

Relevant academic research and scientific papers

Synthesis of 2-mono- and 2,3-disubstituted polycyclic alkenes

A range of mono- and disubstituted (-Br, -Cl, -SPh, -SO2Ph) polycyclic alkenes has been prepared starting from alkenes by inexpensive and high-yielding synthetic routes. ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Bis(arylsulphonyl)acetylenes

Hitherto unknown bis(arylsulphonyl)acetylenes 1 have been prepared via dimethyldioxirane oxidation of the corresponding sulphide; the acetylenes exhibit high reactivity in Diels-Alder and Michael reactions.

(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.