14296-80-1

Usage

Type of compound

Saturated organic compound

Structure

Cyclic alkene with two methylene groups (CH2) attached to a cyclobutane ring

Appearance

Colorless

Flammability

Flammable

Boiling point

49-51°C

Applications

a. Chemical intermediate in the synthesis of various organic compounds and materials
b. Involved in the production of pharmaceuticals, agrochemicals, and polymers
c. Used as a reagent in organic chemistry reactions, particularly in the formation of carbon-carbon bonds

Health hazards

Can pose health hazards if inhaled, ingested, or comes into contact with the skin and eyes

Safety precautions

Should be handled with care in a controlled laboratory setting

InChI:InChI=1/C6H8/c1-5-3-4-6(5)2/h1-4H2

Upstream product

• 463-49-0 1,2-propanediene 
• 342614-33-9 Dimethyl-(2-methylene-cyclobutylmethyl)-amine 
• 1191-95-3 cyclobutanone 
• 1774-47-6 trimethylsulfoxonium iodide 
• 7417-52-9 1,1-trimethyleneallene 
• 74142-72-6 cis-1,2-bis(bromomethyl)cyclobutane 
• 76457-48-2 2-Chlor-3-thiabicyclo<3.2.0>heptan-3,3-dioxid 
• 82253-17-6 trans-1,2-dibromo-1,2-dimethylcyclobutane 
• 107197-40-0 spiro<2.3>hexan-4-one tosylhydrazone 
• 27567-82-4 bicyclopropylidene 
• 18914-34-6 1-methylenespiro[2.2]pentane 
• 1501-58-2 1,2-dimethyl-cyclobutene 
• 30830-20-7 bicyclo<2.2.0>hex-1(4)-ene 

Downstream Products

• 6788-95-0 tricyclo<8.2.0.0^4,7>dodeca-1(10),4(7)-diene 
• 80393-12-0 1-Cyclopropyl-5-(1-cyclopropyl-vinyl)-cyclohexene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 100-40-3 4-ethenylcyclohexene 
• 13898-73-2 1-methyl-5-(1-methylethenyl)cyclohexene 
• 73022-52-3 1,5-dimethyl-1,5-cyclooctadiene 
• 2873-50-9 butatriene 
• 74-85-1 ethene 
• 930-26-7 3-methylene-1-cyclopentene 
• 110-15-6 succinic acid 

Relevant academic research and scientific papers

Novel single step preparation of 2- and 2,3-substituted 1,3-dienes

An efficient method for preparing 2- and 2,3-substituted 1,3-dienes 2, from ketones 1 by treatment with dimethyloxosulfonium methylide in the presence of sodium methylsulfinylmethide is described.

DESHYDROHALOGENATION EN PHASE VAPEUR D' HALOGENURES D' ALKYLES SUR t-BUTYLATE DE POTASSIUM SUPPORTE SUR SILICE: VOIE D' ACCES AUX CYCLES TRES TENDUS

Heterogenous reactions: Highly strained cycloalkenes can be obtained by vapor phase dehydrohalogenation of halocycloalkanes over potassium t-butoxide supported by silica.

Synthesis and properties of the strained alkene perfluorobicyclo[2.2.0]hex-1(4)-ENE

The title fluoroalkene has been generated by dehalogenation of dibromide and diiodide precursors and trapped in situ. retro-Diels-Alder reaction of its adduct with N-benzylpyrrole has made the alkene available in high yield and purity. In sharp contrast t

The thermal transformations of bicyclopropylidene and methylenespiropentane revisited

The overall and the individual rate constants of the unimolecular thermal isomerization of methylenespiropentane (4) to 1,2- and 1,3- dimethylenecyclobutanes (7 and 8) have been determined to be lg(k _4/s_1) = (13.78 ± 0.06) - (49.7 ± 0.2) kcalmol-1/RT·ln10, lg(k7/s-1) = (13.03 ± 0.19) - (48.0 ± 0.6) kcalmo-1/RT·ln10 and lg(k8/s-1) = (14.15 ± 0.19) - (52.4 ± 0.5) kcalmol-1/RT-ln 10, respectively. The activation energies are significantly lower than that for the rearrangement of the parent spiropentane. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Photoisomerization of bicyclopropylidene and 1,2-dimethylenecyclobutane in rare-gas matrices: Towards the IR-spectroscopic identification of tetramethyleneethane (2,3-dimethylenebutane-1,4-diyl)

Bicyclopropylidene (3) and 1,2-dimethylenecyclobutane (7) have been irradiated in rare-gas matrices. If 1,2-dimethylenecyclobutane (7) is exposed to the light of a KrF excimer laser (λ = 248 nm), an isomeric species is produced, showing an absorption at 793.1 cm-1 (argon matrix) or 791.2 cm- 1 (xenon matrix) in the IR spectrum. The back reaction can be induced with light of k λ = 254 nm. This photochemical interconversion, together with the comparison between the experimental and calculated band positions, supports the assignment of the IR absorption near 790 cm-1 to tetramethyleneethane (5).

Hexacyclo[8.7.0.03,8.05,15.06,13.0 12,16]heptadeca-1(10),5-diene-3,8-dicarboxylic anhydride, a tetrahydro[4]beltene with two σ-conjugated double bonds

The tetrahydro[4]beltene 8 has been synthesized via a sequence of three Diels-Alder reactions. As shown in the crystal structure of 8, the two double bonds in the cage diene are positioned face-to-face at a distance of 2.92 A, which is smaller than the sum of their van der Waals radii. The resulting σ-conjugation in 8 is evident from the long wavelength UV adsorption and from the formation of a stable radical cation at low potential. Hydrogenation increases the strain of 8 such that only one double bond can be saturated under forcing conditions.

Forbidden reactions, II. - The disrotatory cyclobutene ringopening

The energy profiles for the con- and disrotatory opening of benzocyclobutene, methylenecyclobutene, and cyclobutene derivatives were established by NO and oxygen trapping. The enthalpy for the transition states for the "forbidden" reactions proofed to be identical with the heat of formation of the orthogonal diradicals derived by geometrical isomerization of the dienes formed in these reactions. These diradicals describe very well the activation barriers observed for the disrotatory opening of bicyclic cyclobutenes ([3.2.0] and [2.2.0] systems), but not for bicyclo[2.1.0]pent-2-ene, indicating here a truly forbidden reaction. VCH Verlagsgesellschaft mbH, 1996.

Alkynes and Cumulenes XXI. - On Some New Oligomers of Allene

The thermal oligomerization of allene (1) in the gas-phase has been reinvestigated.At 260 deg C and low conversion, 1,6,7-trimethylenespirononane (14) and 1,2,5,6-tetramethylenecyclooctane (15) have been detected besides the already known thermal oligomers 2-8.Increase of substrate concentration and reaction time lead to significant amounts of a hexamer fraction which contains the new allene oligomers 16-23 according to spectroscopic analysis.Possible routes of formation of the unusual hexamers 16 and 20 are discussed.

BICYCLOHEX-1(4)-ENE

The preparation of bicyclohex-1(4)-ene (1) via ring expansion of a cyclopropylcarbene or the dehalogenation of 1-bromo-4-chlorobicyclohexane is described.It is one of the most reactive of the alkenes which may be observed at room temperature.Its reactions, including dimerization and cycloaddition reactions, are described.The latter lead to convenient preparations of propellanes.The vibrational spectrum was examined via matrix isolation and ab initio MO calculations.

Synthesis and silver-ion-catalyzed reactions of 3,3'-ethylenebicyclopropenyl

The title compound 2 was obtained from 1,2-dimethylenecyclobutane (1) by double addition of dibromocarbene to give the tetrabromide 9, followed by tin hydride reduction to the dibromide 10 and potassium tert-butoxide elimination of HBr to furnish 2.Silver-ion-catalyzed reaction of 2 did not furnish the expected 1,2- or 1,4-ethylene Dewar benzenes 3 and 4, respectively.Instead, in CDCl3 or dioxane, polymeric material was obtained, while in methanol or methanol-O-d1, opening of one or both cyclopropene rings and addition of methanol gave 11 or 12E/Z, respectively, depending upon the reaction conditions.The two latter compounds provide valuable information about intermediate 13 in the silver-ion-catalyzed rearrangement of bicyclopropenyls to Dewar benzenes.The mechanism of this reaction is discussed.