42860-78-6Relevant 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 (2007/10/03)
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.
Quinone Alkylation Using Organocadmium Reagents: A General Synthesis of Quinols
Aponick, Aaron,McKinley, Jason D.,Raber, Jeffrey C.,Wigal, Carl T.
, p. 2676 - 2678 (2007/10/03)
Reactions of p-benzoquinone with organocadmium reagents yield quinols, the result of quinone carbonyl monoalkylation. The reactions proceed in good yield and are devoid of bisaddition and hydroquinone byproducts. Quinone alkylations using this method show
Organometallic additions to protected quinone bis-epoxides and quinone monoacetals: Synthesis of the aranorosin nucleus
McKillop,Taylor,Watson,Lewis
, p. 1589 - 1591 (2007/10/02)
-