1170718-78-1

Basic information

• Product Name: L-menthol chlorosulfite ester
• Synonyms: L-menthol chlorosulfite ester
• CAS NO: 1170718-78-1
• Molecular Weight: 238.779
• Mol File: 1170718-78-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-menthol chlorosulfite ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-menthol chlorosulfite ester(1170718-78-1)
• EPA Substance Registry System: L-menthol chlorosulfite ester(1170718-78-1)

Safety Data

• Hazardous Substances Data: 1170718-78-1(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 

Downstream Products

• 1228639-20-0 N-[(1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl]-4-chlorobenzamide 
• 1361407-97-7 N-[(1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl]pivalamide 
• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 1147723-25-8 (-)-N-((1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl)benzamide 
• 1361407-96-6 N-[(1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl]-3-phenylpropanamide 
• 34048-59-4 N-[(1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl]acetamide 

Relevant articles and documents

Stereoretentive chlorination of cyclic alcohols catalyzed by titanium(IV) tetrachloride: Evidence for a front side attack mechanism

A mild chlorination reaction of alcohols was developed using the classical thionyl chloride reagent but with added catalytic titanium(IV) chloride. These reactions proceeded rapidly to afford chlorination products in excellent yields and with preference for retention of configuration. Stereoselectivities were high for a variety of chiral cyclic secondary substrates including sterically hindered systems. Chlorosulfites were first generated in situ and converted to alkyl chlorides by the action of titanium tetrachloride which is thought to chelate the chlorosulfite leaving group and deliver the halogen nucleophile from the front face. To better understand this novel reaction pathway, an ab initio study was undertaken at the DFT level of theory using two different computational approaches. This computational evidence suggests that while the reaction proceeds through a carbocation intermediate, this charged species likely retains pyramidal geometry existing as a conformational isomer stabilized through hyperconjugation (hyperconjomers). These carbocations are then essentially "frozen" in their original configurations at the time of nucleophilic capture.

A direct and stereoretentive synthesis of amides from cyclic alcohols

Chlorosulfites prepared in situ using thionyl chloride react with nitrile complexes of titanium(IV) fluoride to give a one-pot conversion of alcohols into amides. For the first time, amides are obtained from cyclic alcohols with stereoretention. Critical to the design of these new TiIV reactions has been the use of little-explored TiIV nitrile complexes that are thought to chelate chlorosulfites in the transition state tocreate a carbocation that is rapidly captured by the nitrile nucleophile through a front-side attack mechanism.