Nishimura, Takahiro published the artcilePalladium-Catalyzed Transformation of Cyclobutanone O-Benzoyloximes to Nitriles via C-C Bond Cleavage, Computed Properties of 4141-48-4, the publication is Journal of Organic Chemistry (2004), 69(16), 5342-5347, database is CAplus and MEDLINE.
Pd-catalyzed transformation of cyclobutanone O-benzoyloximes to a variety of nitriles is described. The reaction may proceed via two important steps, i.e., (i) oxidative addition of the N-O bond of oximes to Pd(0) to give a cyclobutylideneaminopalladium(II) species and (ii) ¦Â-C elimination of this species to afford a reactive alkylpalladium species. The kind of products is very dependent on the nature of substituents on the cyclobutane ring. The direction of the C-C bond cleavage is controlled by the kind of ligand employed. For example, (Z)-2-Allyl-3,3-dibenzylcyclobutanone O-benzoyloxime gave 19/81 and 78/22 2,2-Dibenzyl-4-methylenecyclopentanecarbonitrile and (E)-3,3-Dibenzylhepta-4,6-dienenitrile when two different chiral ligands were used. The sequential reaction composed of the C-C bond cleavage and the subsequent intra- and intermol. C-C bond formations via the corresponding alkylpalladium species is also demonstrated. For example, an oxime having an alkynyl moiety at a suitable position reacts with a variety of alkenes to afford nitriles bearing dienylcyclopentane moiety in moderate to good yields. For example, 50 % [3-[(E,E)-4-(diphenylphosphinyl)-1-phenylbut-2-enylidene]-1-methylcyclopentyl]acetonitrile (characterized by x-ray crystallog.) was obtained from 3-methyl-3-(4-phenylbut-3-ynyl)cyclobutanone O-benzoyloxime and Ph2P(O)CH2CH:CH2 in DMF in the presence of K2CO3, Pd(dba)2 and (R)-BINAP.
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, Computed Properties of 4141-48-4.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia