96133-27-6

Basic information

• Product Name: Cyclohexene, 4-(1,1-dimethylethyl)-1-iodo-
• CAS NO: 96133-27-6
• Molecular Formula: C10H17I
• Molecular Weight: 264.149
• Mol File: 96133-27-6.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Cyclohexene, 4-(1,1-dimethylethyl)-1-iodo-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexene, 4-(1,1-dimethylethyl)-1-iodo-(96133-27-6)
• EPA Substance Registry System: Cyclohexene, 4-(1,1-dimethylethyl)-1-iodo-(96133-27-6)

Safety Data

• Hazardous Substances Data: 96133-27-6(Hazardous Substances Data)

Upstream product

• 62845-83-4 4-(tert-butyl)cyclohex-1-en-1-yl diethyl phosphate 
• 96133-26-5 1-triethylgermyl-4-t-butylcyclohexene 
• 22955-77-7 methyl 1-indanone-2-carboxylate 
• 62082-37-5 hydrazone of 4-tert-butylcyclohexane 
• 77412-96-5 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene 
• 119061-98-2 1-(tributylstannyl)-4-tert-butylcyclohexene 
• 63031-67-4 4-(1,1-dimethylethyl)cyclohexen-1-yltrimethylsilane 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 10442-39-4 tetra-n-butylammonium cyanide 

Downstream Products

• 33800-81-6 4-(tert-butyl)-1-vinyl-1-cyclohexene 
• 33061-20-0 1-(4-tert-butylcyclohex-1-en-1-yl)-4-methoxybenzene 
• 35906-02-6 4-tert-buthyl-1-cyclohexene-1-carboxamide 
• 3419-73-6 1-phenyl-4-tert-butylcyclohexene 
• 273937-88-5 1-(4-tert-butylcyclohex-1-enyl)-2-methylbenzene 
• 2228-98-0 4-tert-butylcylohexene 
• 61187-40-4 4-(tert-butyl)cyclohex-1-enecarbaldehyde 
• 67001-73-4 4-(tert-butyl)cyclohex-1-ene-1-carboxylic acid 
• 1397263-74-9 4-tert-butylcyclohexenyl carboxylic acid phenyl ester 

Relevant articles and documents

Amino- and azidocarbonylation of iodoalkenes

Iodoalkenes, available from ketones via their hydrazones, underwent palladium-catalysed azidocarbonylation. Depending on the structure of the acyl azides, consecutive hydrolysis toward corresponding primary amides was observed. ‘Direct’ aminocarbonylation

Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides

Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)3]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η'1- arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.

Michael addition-elimination mechanism for nucleophilic substitution reaction of cycloalkenyl iodonium salts and selectivity of 1,2-hydrogen shift in cycloalkylidene intermediate

(Chemical Equation Presented) Reactions of cyclohexenyl and cyclopentenyl iodonium salts with cyanide ion in chloroform give cyanide substitution products of allylic and vinylic forms. Deuterium-labeling experiments show that the allylic product is formed via the Michael addition of cyanide to the vinylic iodonium salt, followed by elimination of the iodonio group and 1,2-hydrogen shift in the 2-cyanocycloalkylidene intermediate. The hydrogen shift preferentially occurs from the methylene rather than the methine β-position of the carbene, and the selectivity is rationalized by the DFT calculations. The Michael reaction was also observed in the reaction of cyclopentenyliodonium salt with acetate ion in chloroform. The vinylic substitution products are ascribed to the ligand-coupling (via λ3-iodane) and elimination-addition (via cyclohexyne) pathways.