27538-47-2

Usage

Chemical classification

Bicyclic hydrocarbon

Family

Norbornane family

Applications

a. Ligand in transition metal catalysis
b. Olefin polymerization processes
c. Starting material for organic synthesis
d. Production of specialty chemicals

Physical property

Flammable

Safety precautions

Handle with care in a well-ventilated environment

InChI:InChI=1/C11H18/c1-8-7-9-5-6-11(8,4)10(9,2)3/h9H,1,5-7H2,2-4H3

Upstream product

• 77942-95-1 1,2,3,3-tetramethyl-norbornan-2-ol 
• 78514-53-1 Benzoic acid 1,7,7-trimethyl-2-phenylsulfanylmethyl-bicyclo[2.2.1]hept-2-yl ester 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 76-22-2 Camphor 
• 74-95-3 1,1-dibromomethane 
• 75-09-2 dichloromethane 
• 2371-42-8 1,2,7,7-tetramethylbicyclo<2.2.1>heptan-exo-2-ol 
• 76-22-2 (+)-2-bornanone 
• 19493-09-5 Methylenetriphenylphosphorane 
• 91278-70-5 2-methyl-isoborneol 

Relevant academic research and scientific papers

Dichloromethane activation. Direct methylenation of ketones and aldehydes with CH2Cl2 promoted by Mg/TiCl4/THF

(Chemical Equation Presented) This Mg-TiCl4-promoted CH 2-transfer reaction of CH2Cl2 represents an extremely simple, practical, and efficient methylenation of a variety of ketones and aldehydes, especially in enolizable or sterically hindered ketones such as 2,2-dimethylcyclohexanone, camphor, and fenchone.

Dehydration products of 2-methylisoborneol

2-Methylenebornane and 2-methyl-2-bornene have previously been identified as dehydration or degradation products of 2-methylisoborneol (MIB), a compound responsible for taste and odour problems in various water environments. Previously, the identification of these products has been based on mass spectral analysis only. The dehydration of MIB under a variety of conditions was reinvestigated and the products fully characterised by 1H and 13C n.m.r. and GC-MS. Comparison of EI mass spectra of the dehydration products of MIB with those published previously indicate that earlier assignments of MIB dehydration products are incorrect. 2-Methylenebornane and 2-methyl-2-bornene have previously been identified as dehydration or degradation products of 2-methylisoborneol (MIB), a compound responsible for taste and odour problems in various water environments. Previously, the identification of these products has been based on mass spectral analysis only. The dehydration of MIB under a variety of conditions was reinvestigated and the products fully characterised by 1H and 13C n.m.r. and GC-MS. Comparison of EI mass spectra of the dehydration products of MIB with those published previously indicate that earlier assignments of MIB dehydration products are incorrect.

Intermediate phenolic compounds for the catalytic synthesis of chromans

A catalytic synthesis of chromans in racemic or optically active forms, including intermediates thereto; the synthesis employs an asymmetric palladium (II) catalyzed oxidative cyclization of a 2-homoallylphenol and provides intermediates useful in making chromans, especially vitamin E in racemic or optically active forms.

THE WITTIG REACTION USING POTASSIUM-TERT-BUTOXIDE HIGH YIELD METHYLENATIONS OF STERICALLY HINDERED KETONES

Potassium-tert-butoxide is recommended for general use in Wittig reactions with nonstabilized ylides.High yield methylenations of cyclohexanone and a series of five sterically hindered ketones demonstrate its utility.

Influence of Ring Size on Geminal Interproton Coupling Constants in Exocyclic Methylene Groups

In systems where substituent effects are constant, there is a well defined trend in the magnitude of geminal interproton coupling constants in exocyclic methylene groups with ring size.Reduction of ring size from six to five to four results in a monotonic reduction in the magnitude of Jgem.These trends apply to methylenecycloalkanes, methylenebenzocycloalkenes and α-methylenecycloalkanones.There is an indication that the trend does not continue for methylenecyclopropanes.A number of new exocyclic-methylene compounds have been designed and synthesized to provide specific experimental data.

THE METHYLENATION OF ENOLIZABLE KETONES AND ESTERS USING ORGANOTITANIUM CHEMISTRY

The titanium methylidene fragment, Cp2Ti=CH2, resulting from Tebbe's reagent, Cp2TiCH2*AlMe2Cl or the β,β-disubstituted metallacycle, Cp2TiCH2C(Me)(n-Pr)CH2, methylenates enolizable acidic ketones and converts α,α-disubstituted ketones into titanium enolates.The reagent reacts selectively with ketones over esters.

Wittig-type Reaction of Dimetallated Carbodianion Species as Produced by Zinc Reduction of gem-Polyhalogen Compounds in the Presence of Levis Acids

Treatment of R1COR2 with a suspension prepared from diiodomethane, trimethylaluminium and excess zinc in tetrahydrofuran at room temperature affords olefins R1R2C=CH2 in fair (R1,R2=alkyl) to good (R1=alkyl, R2=H) yields.The ketone methylenation is better carried with another system consisting of CH2Br2-Zn-TiCl4.Ketones and aldehydes are transformed into α-chloro α,β-unsaturated esters or α,β-unsaturated esters in good yields on treatment with methyl trichloroacetate or t-butyl dichloroacetate (ethyl dibromoacetate) in the presence of diethylaluminium chloride and zinc.