196871-46-2Relevant academic research and scientific papers
Regioselective bromomethylation of 1,2-dialkylbenzenes
Garg, Nupur,Lee, T. Randall
, p. 310 - 312 (2007/10/03)
This paper describes a systematic exploration of the regioselective bromomethylation of 1,2-dialkylbenzenes as a function of the reaction temperature and the chain length of the alkyl groups. At both 80 and 110 °C, bromomethyl groups can be introduced into the 4 and 5 positions of 1,2-dialkylbenzenes with high selectivity when the alkyl chains consist of two or more carbon atoms.
Conformational Studies by Dynamic NMR. 62.1 Stereomutations of Rotamers and of Conformational Enantiomers in 1,2-Diacylbenzenes
Casarini, Daniele,Lunazzi, Lodovico,Mazzanti, Andrea
, p. 7592 - 7596 (2007/10/03)
A number of 1,2-diacylbenzenes have been investigated by dynamic NMR spectroscopy. The 1,2-formyl derivative 1 was found to exist (at -162 °C) in the nearly coplanar ZE and EE conformations (70percent and 30percent, respectively) that interconvert with a free energy of activation of 4.9 kcal mol-1. On the contrary, the more hindered 1,2-diisobutanoylbenzene (4) adopts a twisted conformation (as indicated by the 13C spectrum at -157 °C) which, in principle, might correspond either to a meso or to a racemic stereolabile structure. Only the racemic conformer is, however, believed to be populated, and the interconversion barrier between the RR and SS conformational enantiomers has been determined (5.6 kcal mol-1). Although the 1,2-diacetyl- and 1,2-dipropanoylbenzenes did not exhibit dynamic NMR effects in solution, they were assigned a twisted (racemic) conformation on the basis of the corresponding solid state 13C CP-MAS spectra, in that they display a 1:1 doublet signal for each pair of enantiotopic carbons. All these conclusions agree with the predictions of molecular mechanics calculations.
A Novel Cyclization of 1,2-Bis(2,2-dibromocyclopropyl)benzenes with Methyllithium
Hoehn, Juergen,Weyerstahl, Peter
, p. 808 - 814 (2007/10/02)
The CBr2 bis adducts 7, 8, and 10 react with MeLi at - 78 deg C to give the dicyclopropanaphthalenes 17 - 19.Thus, from meso-7 syn-17, and from d,l-7 anti-17 are formed stereoselectively.The reaction may proceed via the intermediates A or B.The carbenoid
