123500-82-3

Upstream product

• 123500-79-8 2-Benzenesulfonyl-3-phenyl-bicyclo[2.2.2]octa-2,5-diene 
• 136964-76-6 2-(2-Methyl-propane-2-sulfonyl)-bicyclo[2.2.2]octa-2,5-diene 
• 2220-40-8 bicyclo[2.2.2]oct-5-en-2-one 
• 123500-76-5 2,3-Bis-benzenesulfonyl-bicyclo[2.2.2]octa-2,5-diene 
• 123500-76-5 (1S,4R)-2,3-Bis-benzenesulfonyl-bicyclo[2.2.2]octa-2,5-diene 
• 123500-79-8 (1S,4R)-2-Benzenesulfonyl-3-phenyl-bicyclo[2.2.2]octa-2,5-diene 
• 132555-56-7 5,6-Bis-benzenesulfonyl-5-chloro-bicyclo[2.2.2]oct-2-ene 
• 80871-94-9 5-phenylbicyclo<2.2.2>oct-2-en-5-ol 
• 925-90-6 ethylmagnesium bromide 
• 136964-78-8 2-(2-Methyl-propane-2-sulfonyl)-3-phenyl-bicyclo[2.2.2]octa-2,5-diene 

Relevant academic research and scientific papers

BIS(TERT-BUTYLSULFONYL)ACETYLENE AS A GENERAL SYNTHETIC EQUIVALENT OF ALKYNES IN DIELS-ALDER CHEMISTRY. II: REDUCTIVE AND ALKYLATIVE DESULFONYLATIONS OF BICYCLIC 1-ALKYL-2-(TERT-BUTYLSULFONYL)ETHENES

Both reductive and alkylative desulfonylations of bicyclic vinyl sulfones derived from Diels-Alder cycloadducts of bis(tert-butylsulfonyl)acetylene (1) are described.These transformations establish the synthetic equivalence of 1 with acetylene, 1-alkynes

(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.

The Triplex Diels-Alder Reaction of 1,3-Dienes with Enol, Alkene, and Acetylenic Dienophiles: Scope and Utility

The cycloaddition of an electron-rich diene to an electron-rich dienophile may be catalyzed by irradiation of a cyanoarene.This reaction is shown to proceed through an intermediate ternary excited state complex (triplex) and is therefore called th