84784-46-3

Basic information

• Product Name: trans-3-t-butylcyclohexanecarbonitrile
• CAS NO: 84784-46-3
• Molecular Weight: 165.279
• Mol File: 84784-46-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: trans-3-t-butylcyclohexanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-t-butylcyclohexanecarbonitrile(84784-46-3)
• EPA Substance Registry System: trans-3-t-butylcyclohexanecarbonitrile(84784-46-3)

Safety Data

• Hazardous Substances Data: 84784-46-3(Hazardous Substances Data)

Upstream product

• 19123-26-3 (+/-)-toluene-4-sulfonic acid-(cis-3-tert-butyl-cyclohexyl ester) 
• 143-33-9 sodium cyanide 
• 2228-98-0 4-tert-butylcylohexene 
• 74-90-8 hydrogen cyanide 

Relevant articles and documents

Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1-Methylcyclohexa-2,5-diene-1-carbonitrile

Catalytic transfer hydrocyanation represents a clean and safe alternative to hydrocyanation processes using toxic HCN gas. Such reactions provide access to pharmaceutically important nitrile derivatives starting with alkenes and alkynes. Herein, an efficient and practical cooperative palladium/Lewis acid-catalyzed transfer hydrocyanation of alkenes and alkynes is presented using 1-methylcyclohexa-2,5-diene-1-carbonitrile as a benign and readily available HCN source. A large set of nitrile derivatives (>50 examples) are prepared from both aliphatic and aromatic alkenes with good to excellent anti-Markovnikov selectivity. A range of aliphatic alkenes engage in selective hydrocyanation to provide the corresponding nitriles. The introduced method is useful for chain walking hydrocyanation of internal alkenes to afford terminal nitriles in good regioselectivities. This protocol is also applicable to late-stage modification of bioactive molecules.

THE STEREOCHEMISTRY OF METAL CATALYSED HYDROGEN CYANIDE ADDITION TO ALKENES

Reaction of both terminal and cyclic alkenes have been shown to occur in a stereospecifically cis-manner with deuterium cyanide when a catalyst system based on Pd(DIOP)2 was used.Reactions of cyclohexene give only the products of equatorial cyanide incorporation.