3141-45-5

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 87, p. 4147, 1965 DOI: 10.1021/ja01096a025The Journal of Organic Chemistry, 47, p. 1587, 1982 DOI: 10.1021/jo00347a047

InChI:InChI=1/C7H12Cl2/c1-5(2)6(3,4)7(5,8)9/h1-4H3

Upstream product

• 563-79-1 2,3-Dimethyl-2-butene 
• 1605-72-7 dichlorocarbene 
• 67-66-3 chloroform 
• 15113-10-7 Essigsaeure-trichlormethylester 
• 650-51-1 sodium trichloroacetate 
• 633303-45-4 3,3-dichloro-2,2,4,4-tetramethylcyclobutan-1-one 
• 56-23-5 tetrachloromethane 
• 5936-98-1 trichloromethyltrimethylsilane 
• 121410-82-0 1,1-Dibromo-2,2-dichloro-3-methoxymethyl-3-methyl-cyclopropane 
• 115-11-7 isobutene 
• 848768-04-7 3-chloro-3-(p-nitrophenoxy)diazirine 
• 86170-93-6 3,3-dichlorodiazirine 
• 126191-47-7 pyridinium dichloromethyl ylide 

Downstream Products

• 4127-47-3 2,2,3,3-tetramethylcyclopropane 
• 14123-41-2 1-Chloro-2,2,3,3-tetramethylcyclopropane 
• 85036-31-3 2,2,2',2',3,3,3',3'-Octamethyl-1,1'-bi(cyclopropyliden) 
• 28569-96-2 1,2,2-Trimethylbicyclo<1.1.0>butan 
• 110079-18-0 9-(2,2,3,3-Tetramethylcyclopropyl)-9,10-dihydroanthracen 
• 110079-19-1 9,10-Bis(2,2,3,3-tetramethylcyclopropyl)-9,10-dihydroanthracen 
• 3422-07-9 1-isopropenyl-1-methylcyclopropane 

Relevant academic research and scientific papers

The synthesis of dichlorodiazirine and the generation of dichlorocarbene: Spectroscopy and structure of dichlorocarbene ylides

Reaction of 2,4-dinitrophenoxychlorodiazirine (13) with chloride ions affords dichlorodiazirine (4). Photolysis of 4 generates dichlorocarbene. In laser flash photolysis (LFP) experiments, CCl2 forms chromophoric ylides or oxides with pyridine,

Kinetics and mechanism of CCU photoreductive degradation on TiOi: The role of trichloromethyl radical and dichlorocarbene

The mechanism of photoreduction of CCU on illuminated TiO2 surfaces was investigated by selectively trapping transient free radical intermediates. Dichlorocarbene and trichloromethyl radical were trapped with 2,3dimethyl-2-butene during the photocatalytic degradation of CCLt. The rate of formation of trapped :CCl2 and 'CCla was found to be a function of [H22O], pH, [CCLt], the nature of the dissolved gas, and light intensity. Dissolved oxygen was not essential for the degradation of CCLt. The production rate of trapped dichlorocarbene showed light intensity dependencies of second, first, and half order with progressively increasing light intensity. A two-electron photoreductive pathway (via dichlorocarbene formation) was found to be the dominant mechanism leading to the full degradation of CCLt. Since dichlorocarbene is hydrolyzed under basic conditions, the pH and water concentration were found to be integral parameters controlling the complete degradation of CCU to CO, CU2, and HC1. Kinetic equations describing the formation of trapped dichlorocarbene were derived from a proposed mechanism. The comparison of the predicted rate expression to the observed data suggested that the observed two-electron transfer occurred consecutively.

α-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid

2,2,3,3-Tetramethylcyclopropanecarboxylic acid (TMCA, 4) is a cyclic analogue of the antiepileptic drug (AED) valproic acid (VPA) (1). α-F, α-Cl, R-Br, and R-methyl derivatives of 4 and their amides were synthesized and tested in rodent models for anticonvulsant potency and AED-induced teratogenicity. In the anticonvulsant rat-maximal electroshock (MES) and subcutaneous metrazol (scMet) tests, α-Cl-TMCD (17) had ED 50 values of 97 and 27 mg/kg, respectively. α-F-TMCD (11) was 120 times more potent than VPA in the rat-scMet test (ED50) 6 mg/kg) and had a protective index (PI) TD50/ED50) of 20. In the 6 Hz psychomotor mouse model 11 had ED50 values of 57 mg/kg (32 mA) and 59 mg/kg (44 mA). The ED50 values of 11 in the hippocampal-kindled rat model and in the pilocarpine-induced-status rat model were 30 and 23 mg/kg, respectively. Unlike 1, 11 was nonteratogenic in mice. This novel compound has the potential to become a candidate for development as a new potent and safe antiepileptic and CNS drug.

ALPHA-HALO- AND ALPHA-ALKYL-CYCLOPROPYLCARBOXY COMPOUNDS AND USES THEREOF

Novel Alpha-halo- and Alpha-alkyl-cyclopropylcarboxy compounds, and uses of these and related compounds in the treatment of a variety of neurological diseases and disorders, and particularly epilepsy, are provided.

Enthalpy versus entropy in chlorocarbene/alkene addition reactions

We report the first measured activation parameters for the additions of CCl2 and CClF to simple alkenes and demonstrate the existence of enthalpic barriers for CCl2 additions to cyclohexene and 1-hexene. With these two alkenes, addit

Is a phase transfer catalyst really needed for gem-dihalocyclopropanation of alkenes with haloforms in the presence of alkali metal hydroxide?

Chloroform, bromoform and dibromochloromethane react with alkenes in the presence of cone. aq. sodium hydroxide, without phase-transfer catalyst, giving gem-dihalocyclopropanes. The process is particularly useful for preparation of gem-bromochlorocyclopropanes which are formed in good yields and in high selectivity.

Dichlorodiazirine: A nitrogenous precursor for dichlorocarbene

The reaction of 3-p-nitrophenoxy-3-chlorodiazirine with a 1.1:1.0:1.6 blend of tetrabutylammonium chloride, cesium chloride, and the ionic liquid 1-butyl-3-methylimidazolium chloride at 40-50 °C under vacuum at 1 mm·Hg produced a melt from which dichlorod

A search for dichlorocarbene ether solvent interactions

The absolute rate constant of reaction of dichlorocarbene with pyridine and with tetramethylethylene was determined in Freon-113 (CF2ClCFCl2), dioxane, and tetrahydrofuran. No evidence of specific solvation was obtained.

gem-Dihalocyclopropane formation by iron/copper activation of tetrahalomethanes in the presence of nucleophilic olefins. Evidence for a carbene pathway

The activation of CBr4 and CCl4 by a bimetallic iron/copper couple in acetonitrile is a new, inexpensive, nontoxic and efficient procedure for gem-dibromo- and gem-dichloromethylenation of nucleophilic alkenes. This new route to gem-dihalocyclopropanes involves dihalocarbene species.