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Oxidation of Cycloalkenes and Methylenecycloalkanes by Palladium(II) Complexes. Part 2. NMR Study on the Mechanism of the Ring Expansion of Methylenecyclobutane Full article

Общее Language: Английский, Genre: Full article,
Status: Published, Source type: Original
Journal Journal of Molecular Catalysis (Continued after 1994 as Journal of Molecular Catalysis A: Chemical and Journal of Molecular Catalysis B: Enzymatic)
ISSN: 0304-5102
Output data Year: 1993, Volume: 83, Number: 3, Pages: 301-310 Pages count : 10 DOI: 10.1016/0304-5102(93)87040-F
Tags cycloalkene oxidation, methylenecyclobutane, oxidation, palladium
Authors Beck I.E. 1 , Gusevskaya E.V. 1 , Golovin A.V. 1 , Likholobov V.A. 1
Affiliations
1 Boreskov Institute of Catalysis

Abstract: The reaction of methylenecyclobutane (1) with bis(acetonitrile)chloronitropalladium(II) in methylene chloride yields cyclopentanone. Two intermediates - π-olefin complex of palladium and product of β-nitritopalladation of 1 in a Markovnikov fashion - are observed by 1H and 13C NMR. Palladium-catalyzed ring expansion of 1 is suggested to involve heterolysis of the palladium-carbon bond and rearrangement of the resulting cyclobutyl to cyclopentyl cations. The selective formation of ring-expanded and ring-contracted carbonyl products from methylenecyclobutane and 1-methyleyclobutene, respectively, is discussed in terms of proposed mechanism.
Cite: Beck I.E. , Gusevskaya E.V. , Golovin A.V. , Likholobov V.A.
Oxidation of Cycloalkenes and Methylenecycloalkanes by Palladium(II) Complexes. Part 2. NMR Study on the Mechanism of the Ring Expansion of Methylenecyclobutane
Journal of Molecular Catalysis (Continued after 1994 as Journal of Molecular Catalysis A: Chemical and Journal of Molecular Catalysis B: Enzymatic). 1993. V.83. N3. P.301-310. DOI: 10.1016/0304-5102(93)87040-F publication_identifier_short.wos_identifier_type publication_identifier_short.scopus_identifier_type publication_identifier_short.rinz_identifier_type
Dates:
Submitted: Sep 10, 1992
Accepted: Mar 20, 1993
Published print: Jul 30, 1993
Published online: Oct 2, 2001
Identifiers:
publication_identifier.wos_identifier_type WOS:A1993LQ32700004
publication_identifier.scopus_identifier_type 2-s2.0-0027626237
publication_identifier.rinz_identifier_type 31642004
publication_identifier.accession_number_identifier_type 1994:30336
publication_identifier.chemical_accession_number_identifier_type 120:30336
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