2349-70-4Relevant articles and documents
Experimental and semiemprical studies of chemical reactivity of dialkylcadmium reagents addition to α,β-enones
Ghandi, Mehdi,Shahidzadeh, Mansour
, p. 4918 - 4925 (2006)
Experimental and semiempirical calculations were carried out to study the reactivity of dialkylcadmium reagents addition to α,β-enones. It was demonstrated that α,β-enone such as benzoquinone with low lying LUMO energy reacts via single electron transfer (SET) mechanism with the formation of the 1,2 or 1,4-type alkyl addition product depending on the reaction temperature and substrate structure. Site and chemoselectivity in unsymmetrical benzoquinone derivatives are determined by the stability of the cadmium coordinated semienone complex intermediates and the carbon spin densities of these reactive species respectively. On the other hand, by increasing the LUMO energy of α,β-enone system, the reaction mechanism changes from SET to polar addition affording the 1,4-type alkyl addition product. The establishment of a correlation scale between substrate LUMO energies and reaction mechanism presented in this article will be discussed.
-
Florjanczyk,Z. et al.
, p. 21 - 28 (1976)
-
Candida antarctica lipase B-mediated regioselective acylation of dihydroxybenzenes in organic solvents
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei,Maeda, Yuki
, p. 3915 - 3923 (2015/06/02)
Candida antarctica lipase B proved to be a highly active biocatalyst for the direct acylation of phenolic hydroxy groups of substituted hydroquinones and resorcinols, which have rarely been reported so far. More importantly, the acylation reactions took place generally in a markedly regioselective manner: the hydroxy group remote from the substituent was preferentially acylated. In the case of substituted hydroquinones, the selectivity increased with the increase in the bulk of the substituent. Interestingly, the 1-O-monoacylated derivatives were obtained as the sole products in the case of 4-substituted resorcinols.
Re2O7 catalyzed dienone-phenol rearrangement
Xia, Zilei,Hu, Jiadong,Shen, Zhigao,Yao, Qizheng,Xie, Weiqing
, p. 38499 - 38502 (2015/06/24)
The dienone-phenol rearrangement of 4,4-disubstituted cyclohexadienones catalyzed by Re2O7 has been described. Multi-substituted phenols can be efficiently obtained in good to excellent yields by employing this catalytic protocol.