94625-86-2

Upstream product

• 253185-03-4 tert-butylbenzene 
• 2495-32-1 4,4-dimethyl-3-methylenepent-1-ene 
• 152272-68-9 bis(9-borabicyclo{3.3.1}non-9-yl)acetylene 
• 109297-56-5 trans-1-(9-borabicyclo<3.3.1>non-9-yl)-2-(trimethylsilyl)ethene 

Downstream Products

• 1498315-19-7 C₁₀H₁₆O 
• 1498315-20-0 C₁₀H₁₆O 

Relevant academic research and scientific papers

Isotope effects and the distinction between synchronous, asynchronous, and stepwise Diels-Alder reactions

A variety of symmetrical or nearly symmetrical Diels-Alder reactions are studied by a combination of experimental isotope effects, theoretical calculations, and rate observations. Becke3LYP calculations predicted highly asynchronous transition structures for Diels-Alder reactions of bis(boryl)acetylenes, dialkyl acetylenedicarboxylates, triazolinediones, and dialkyl maleates. Rate observations and kinetic isotope effects are consistent with these predictions, though the experimental support for the calculated structures is notably ambiguous in some cases. A concerted mechanism is supported for the retro-Diels-Alder reaction of norbornene. Overall, Diels-Alder reactions appear to be only very weakly biased toward synchronous transition states.

Catalysis by temporary covalent activation. A novel catalysis of unactivated Diels-Alder reactions

Diels-Alder reactions of cis-2-chlorovinyltributylstannane are greatly accelerated by the presence of catalytic amounts of haloboranes. Mechanistic studies support a mechanism for the catalysis involving an intermediate boron-aclivated dienophile. A simil

2-Trimethylsilylvinylboranes: Highly reactive and selective Diels-Alder equivalents of 2-trimethylsilylvinyl alcohol and acetylene

The readily available 2-trimethylsilylvinyl-9-BBN (1) is a highly reactive and selective dienophile. The Diels-Alder products are easily converted into trimethylsilylcyclohexenols and 1,4-cyclohexadienes.

Composition of Mixtures of Hydrocarbons after BIRCH-Reduction of Substituted Benzenes and Acid Catalyzed Addition of Alcohols to Alkylsubstituted Cyclohexenes and Carbohexa-1,4-dienes

10 different benzene hydrocarbons 1, indane, tetraline, anisol and phenol are reduced by sodium in liquid ammonia in the presence of methanol to the BIRCH products 2.The product mixture compositions are determined through capillary GLC.On storage at +6 deg C some rearomatization of the 1,4-cyclohexadienes 2 occurs.Data of the 1H- and 13C-.n.m.r. spectra and also mass spectra of the BIRCH 1,4-dienes 2 are given.For comparison 4-alkoxycyclohexenes 4 and 1-alkoxy-1-methylcyclohexanes 8 are prepared and spectroscopically characterized.Acid-catalyzed addition of alcohols to the 1,4-cyclohexadienes systems is a slow process and gives the 4-alkoxy-4-alkylcyclohex-1-enes (4) only in moderate yields up to 30percent.Most of the products are dimers 5 and also oligomers 6 of the parent hydrocarbons 2.

Novel Dimerisation Reaction of Hydrocarbons with Cs-K-Na Alloy

m-Xylene undergoes dimerisation with Cs-K-Na alloy at -48 deg C to give 1,1',4,4'-tetrahydro-3,3',5,5'-tetramethylbiphenyl (3) while o- and p-xylenes do not follow such a reaction under identical conditions.