Padwa, Albert published the artcileRhodium(II)-catalyzed cyclization reactions of alkynyl-substituted ¦Á-diazo ketones, Safety of Allyldiphenylphosphine oxide, the publication is Journal of Organic Chemistry (1991), 56(7), 2523-30, database is CAplus.
Treatment of several o-alkynyl-substituted ¦Á-diazoacetophenone derivatives with rhodium(II) carboxylates results in the formation of substituted indenones. The simplest mechanism accounting for the results involves addition of a rhodium-stabilized carbenoid onto the acetylenic ¦Ð-bond to generate a vinyl carbenoid directly or possibly a highly strained cyclopropene derivative The vinyl carbenoid was found to undergo addition to a neighboring alkene tethered on the side chain to give an indenyl-substituted bicyclo[3.1.0]hexane derivative A number of related systems were examined so as to probe the scope and generality of the process. Treatment of 2-[CH2:CHCH:CH(CH2)3Cú·C]C6H4COCHN2 with rhodium(II) mandelate afforded a benzocyclopent[g]azulenone derivative I. The formation of this compound involves a divinylcyclopropane intermediate that readily undergoes a Cope rearrangement under the reaction conditions. The rhodium-catalyzed reaction of 2-[MeCO(CH2)3Cú·C]C6H4COCHN2 in the presence of N-phenylmaleimide afforded a mixture of two cycloadducts II and III. Product II can be accounted for in terms of a cyclization of the vinyl carbenoid onto the oxygen atom of the neighboring carbonyl group to give a resonance-stabilized dipole. 1,3-Dipolar cycloaddition of the carbonyl ylide across the activated ¦Ð-bond of N-phenylmaleimide affords the observed product. The structure of II was confirmed by x-ray anal. The second cycloadduct III is formed by a 1,2-hydrogen shift of the initially produced vinyl carbenoid. The resulting diene undergoes a subsequent Diels-Alder reaction with N-phenylmaleimide.
Journal of Organic Chemistry published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Safety of Allyldiphenylphosphine oxide.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia