27770-83-8

Basic information

• Product Name: endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene
• Synonyms: endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene
• CAS NO: 27770-83-8
• Molecular Weight: 374.482
• Mol File: 27770-83-8.mol

Chemical Properties

• CAS DataBase Reference: endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene(27770-83-8)
• EPA Substance Registry System: endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene(27770-83-8)

Safety Data

• Hazardous Substances Data: 27770-83-8(Hazardous Substances Data)

Upstream product

• 27770-82-7 (1RS)-5endo,6endo((RS,RS)-bis-benzenesulfinyl)-norborn-2-ene 
• 97760-26-4 2,3-bis(phenylsulphonyl)bicyclo<2.2.1>hepta-2,5-diene 
• 542-92-7 cyclopenta-1,3-diene 
• 963-15-5 (Z)-1,2-bis(phenylsulfonyl)ethene 

Downstream Products

• 88197-34-6 2-exo,3-endo-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 

Relevant articles and documents

DICHOTOMY IN THE DOUBLE BOND REACTIVITY OF 2,3-BIS(PHENYLSULPHONYL)BICYCLOHEPTA-2,5-DIENE AND RELATED COMPOUNDS

Selctivity between the two double bonds of the title compound, 2, has been observed for a number of reagents.For example, cycloaddition with cyclopentadiene and anthracene, as well as reduction with molecular hydrogen (under palladium catalysis), took place at the unsubstituted double bond, while cyclohexadiene, α-terpinene and benzenethiol gave reduction (uncatalyzed) at the more substituted bond.The same reactions performed on the related substrate 3,4-bis(phenylsulphonyl)tricyclo2,4>nona-3,7-diene, 3, afforded comparable results, except for the reaction with cyclopentadiene, which resulted in the cycloaddition to the sulphonyl-activated double bond.

(Z)- and (E)-1,2-Bis(phenylsulfonyl)ethylenes as Synthetic Equivalents to Acetylene as Dienophile

A new method for introducing an ethylenic bridge via a cycloaddition reaction has been developed.It makes use of either (Z)- or (E)-1,2-bis(phenylsulfonyl)ethylene (5 or 6) as synthetic equivalents of acetylene.The high activation due to the two sulfonyl groups promotes cycloaddition even to very unreactive dienes.The removal of the two sulfonyl groups for the required formation of the carbon-carbon double bond is promoted by reduction with metal amalgams in high yields.These properties, associated with the stability of the reagents and the ease of performance of the reactions, make this method a very useful synthetic tool for the preparation of polycyclic dienes and a valid alternative to the commonly available reagents that largely depend upon oxidative methods.

cis-1,2-Bis(phenylsulfonyl)ethylene: a Novel, Convenient Acetylene Synthon in Diels-Alder Reactions

cis-1,2-Bis(phenylsulfonyl)ethylene (5) is found to be a reactive acetylene synthon in Diels-Alder reactions since, after cycloaddition to cyclopentadiene, cyclohexadiene, and cycloheptatriene, and reduction with sodium amalgam, the corresponding bicyclodienes (6)-(8) are obtained in good yields.