23904-34-9

Basic information

• Product Name: (1-Iodomethylene)cyclopentane
• Synonyms: (1-Iodomethylene)cyclopentane
• CAS NO: 23904-34-9
• Molecular Weight: 208.042
• Mol File: 23904-34-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1-Iodomethylene)cyclopentane(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Iodomethylene)cyclopentane(23904-34-9)
• EPA Substance Registry System: (1-Iodomethylene)cyclopentane(23904-34-9)

Safety Data

• Hazardous Substances Data: 23904-34-9(Hazardous Substances Data)

Upstream product

• 85390-84-7 (Diiodomethyl)cyclopentane 

Downstream Products

• 177-10-6 1,3-dioxolane-2-spirocyclohexane 
• 1528-30-9 methylenecyclopentane 
• 930-66-5 1-chlorocyclohexene 
• 1384172-77-3 C₁₂H₁₃ClS 
• 1384172-78-4 (4-chlorophenyl)(cyclopentenylmethyl)sulfane 

Relevant articles and documents

Photochemistry of Alkyl Halides. 9. Geminal Dihalides

The photobehavior of the geminal dihalides (diiodomethyl)cyclohexane (7), (bromoiodomethyl)cyclohexane (11), (dibromomethyl)cyclohexane (17), (diiodomethyl)cyclopentane (22), 3,3-dimethyl(diiodomethyl)cyclobutane (27), and 8,8-diiodo-2,6-dimethyl-2-octene (31) has been studied and compared with that previously observed for diiodomethane.In all solvents the corresponding vinyl halides (iodomethylene)cyclohexane (13), (bromomethylene)cyclohexane (21), (iodomethylene)cyclopentane (23), 3,3-dimethyl(iodomethylene)cyclobutane (28), or cis- and trans-3,7-dimethyl-1-iodo-1,6-octadiene (33) were obtained, which are thought to arise from α-halo cationic intermediate formed via initial light-induced homolytic cleavage of the carbon-iodine bond followed by electron transfer within the resulting caged radical pair, as shown in Schemes II and III.In the case of diiodide 31 competing intramolecular trapping of the α-iodo cation afforded in addition the cyclized isopulegyl iodide (34).In polar solvents the vinyl iodides were accompanied by the nonhalogenated products methylenecyclohexane (15), 1-methylcyclopentene (25), cyclohexene (26), 4,4-dimethylcyclopentene (29), and cis- and trans-carane (35), which are thought also to arise from the α-halo cationic intermediate. 1.1-Diiodo-2,2-dimethylpropane (1b) afforded 2-methyl-2-butene (6b).Except for carane (35) from diiodide 31 there was no detectable formation of cyclopropanes.In methanol the nucleophilic substitution products (dimethoxymethyl)cyclohexane (14), (dimethoxymethyl)cyclopentane (24), and 1,1-dimethoxy-2,2-dimethylpropane (30) were obtained.It is concluded that geminal dihalides undergo predominant, if not exclusive, photoreaction via initial clea vage of a single carbon-halogen bond in analogy with monohalides and that carbene intermediates are not formed.A similiar conclusion has been reached previously for diiodomethane in the photocyclopropanation of alkenes.