90534-01-3

Upstream product

• 3048-65-5 cis-bicyclo<4.3.0>nona-3,7-diene 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 56170-01-5 cis-bicyclo<4.3.0>nona-2,7-diene 

Downstream Products

• 53403-88-6 (-)-δ-lactone of 3-epi-cucurbic acid 
• 58240-50-9 cucurbic acid 
• 139448-28-5 (+)-(1R,2S,3R)-methyl 3-hydroxy-2-(2-triphenylmethoxyethyl)-1-cyclopentaneacetate 
• 139448-30-9 (+)-(1R,2S,3S)-methyl 3-acetoxy-2-(2-triphenylmethoxyethyl)-1-cyclopentaneacetate 
• 139560-24-0 (-)-(1R,2S,3R)-methyl 3-acetoxy-2-(2-triphenylmethoxyethyl)-1-cyclopentaneacetate 
• 139448-29-6 [(1R,2S,3R)-3-Methanesulfonyloxy-2-(2-trityloxy-ethyl)-cyclopentyl]-acetic acid methyl ester 
• 110840-55-6 ((3aS,7aS)-3-Oxo-1,2,3,4,7,7a-hexahydro-inden-3a-yl)-phenylsulfanyl-acetic acid methyl ester 
• 110840-55-6 ((3aS,7aR)-3-Oxo-1,2,3,4,7,7a-hexahydro-inden-3a-yl)-phenylsulfanyl-acetic acid methyl ester 

Relevant academic research and scientific papers

ISOMERIC CIS-BICYCLONONADIENES

cis-Bicyclonona-2,7-dienes and the corresponding 2,8-dienes were obtained by the isomerization of cis-bicyclonona-3,7-diene and dehydration of the cis-bicyclonon-7(8)-en-3-ols.The 13C and PMR spectra of the isomeric dienes were investigated, and their retention times in GLC analysis were determined.The reaction of cis-bicyclonona-3,7-diene with N-bromosuccinimide in aqueous DMSO and the reaction of cis-bicyclonona-2,7-diene with acetic acid were studied.

ADDITION OF HYDROGEN BROMIDE TO CIS-BICYCLONONA-3,7-DIENE. SYNTHESIS OF 5-BROMOBREXANE AND BREXAN-5-ONE

The addition of hydrogen bromide to cis-bicyclonona-3,7-diene takes place preferentially but not selectively at the double bond of the six-membered ring.In the case of gaseous hydrogen bromide only bromobicyclononenes are formed, but with 48percent aqueous hydrobromic acid the reaction is accompanied by transannular cyclization and by the formation of endo- and exo-5-bromobrexanes (16-20percent).A method is proposed for the production of brexan-5-one.