53829-23-5

Upstream product

• 108-05-4 vinyl acetate 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 33475-09-1 1,2-dimethyl-1-cyclohexen-4-one 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 754-05-2 ethenyltrimethylsilane 
• 3677-80-3 dichlorovinylborane 
• 10147-87-2 dibromovinylborane 
• 43087-42-9 4-methoxy-1,2-dimethyl-1,4-cyclohexadiene 
• 75927-49-0 pinacol vinylboronate 

Downstream Products

• 103723-86-0 C₉H₁₃ClO₂ 
• 53829-24-6 1,2-dimethyl-1-cyclohexen-4-yl tosylate 
• 236752-33-3 3,4-dimethylcyclohex-3-enol mesylate 
• 1674-10-8 1,2-dimethylcyclohexene 
• 17351-28-9 1,2-dimethyl-1,4-cyclohexadiene 
• 103723-87-1 3,4-dimethylcyclohex-3-enyl N-hydroxycarbamate 
• 103723-88-2 3-(3,4-dimethylcyclohex-3-enyloxycarbonyl)-2-oxa-3-azabicyclo<2.2.1>hept-5-ene 

Relevant academic research and scientific papers

A facile microwave-assisted Diels-Alder reaction of vinylboronates

The Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.

Syntheses with organoboranes. IX. Vinyl- and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels-Alder reaction

Vinyl- and 1-alkenyldichloroboranes were used as dienophiles for the Diels-Alder reaction with representative aliphatic and cyclic 1,3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation-mesylation-reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride produced pure olefins in good yields.

In situ formation of alkenyl- and alkynylboranes for Diels-Alder reactions by boron-silicon exchange with alkenyl- and alkynylsilanes

A variety of alkenylsilanes underwent transmetallation with BBr3 to afford the corresponding alkenyldibromoboranes in solution. Similarly, the transmetallation of alkynylsilanes with BCl3 afforded alkynyldichloroboranes, A number of the alkenyl- and alkynylboranes are novel and useful Diels-Alder dienophiles. An ionic mechanism for the transmetallation is proposed.

Factors Influencing Conformational Preferences in Cyclohexenes

Conformational preferences have been measured for the first time for 4-substituted cyclohexenes in a solvent of low polarity.Measurements were made for the substituents Cl, Br, I, OH, OSiMe3, and CN and were compared with conformational preferences in cyclohexyl and exo-methylenecyclohex-3-yl.In the nearly nonpolar solvent CF2Cl2, in which intramolecular interactions are maximized, there is a much larger axial population for cyclohexen-4-yl than in cyclohexyl or exo-methylenecyclohex-3-yl.In particular, the dipolar interaction of the endocyclic double bond is reduced from that of the exocyclic double bond.This observation is confirmed by the almost negligible effect of symmetrizing the endocyclic double bond through 1,2-dimethyl substitution, in contrast with the large effect of symmetrizing the exocyclic double bond through 7,7-dimethyl substitution.Polar solvents increase the proportion of the axial conformer to a smaller extent for the endocyclic than for the exocyclic system, again in agreement with a lower dipolar effect in the endocyclic case.These results emphasize the anisotropic nature of the steric effects of double bonds.