57199-09-4

Basic information

• Product Name: (1R,3R,6R,7S,9S)-5-Oxo-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid methyl ester
• CAS NO: 57199-09-4
• Molecular Weight: 196.203
• Mol File: 57199-09-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,3R,6R,7S,9S)-5-Oxo-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R,6R,7S,9S)-5-Oxo-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid methyl ester(57199-09-4)
• EPA Substance Registry System: (1R,3R,6R,7S,9S)-5-Oxo-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid methyl ester(57199-09-4)

Safety Data

• Hazardous Substances Data: 57199-09-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 39589-98-5 endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic dimethyl ester 
• 4582-20-1 5-oxo-4-oxatricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid 
• 57199-09-4 endo-3-methoxycarbonyl-2,6-norbornanecarbolactone 

Downstream Products

• 57199-09-4 (+/-)-5endo-hydroxy-norbornane-2exo,3endo-dicarboxylic acid-3-lactone-2-methyl ester 

Relevant articles and documents

Fluorolactonization of norbornenecarboxylic acids and their methyl esters with F-TEDA-BF4 and XeF2

The selective fluorolactonization was achieved by treatment of cis-5-norbornene-2,3-endo-dicarboxylic acid or its monomethyl and dimethyl esters with F-TEDA-BF4 or XeF2. The reactions of 5-norbornene-endo-2-carboxylic acid and its monomethyl ester with F-TEDA-BF 4 or XeF2 proceed in a non-selective manner to give fluorolactonization, addition and rearrangement products. The basic factor responsible for selectivity of the fluorolactonization is the presence of two endo-oriented carboxyl groups in the substrate molecule. The electrophilicity and type of the fluorinating agent is of secondary importance in this regard. It is postulated that the fluorolactonization of norbornenecarboxylic acids and their methyl esters with F-TEDA-BF4 or XeF2 is realized mainly via "open" fluoronorbornyl carbocation intermediates which in the reaction with XeF2 are postulated as the tight ion pairs.