Oxidative rearrangements of tricyclic vinylcyclobutane derivatives

Grota J, Mattay J, Piech K, Bally T (2006)
CHEMISTRY-A EUROPEAN JOURNAL 12(17): 4559-4567.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Grota, J; Mattay, JochenUniBi; Piech, K; Bally, T
Abstract / Bemerkung
Three tricyclic vinylcyclobutanes (3-methylenetricyclo[5.3.0.0(2,6)]-decanes 1-3) have been subjected to ionization by photoinduced electron transfer in solution and by X-irradiation in Ar matrices. All three compounds undergo oxidative cycloreversion; the cleavage of the four-membered ring, however, occurs in a different direction depending on the presence of a methyl group in position 6 of the tricyclic framework. In those derivatives, cycloreversion is found to lead to 1-methyl-8-methylene-1,6-cyclodecadiene radical cations (5(.+) from 1, 8(.+) from 2) which upon back electron transfer yield two different hydrocarbons (6 from 5(.+), 9 from 8(.+)), depending on the configuration around the endocyclic double bonds of the respective cyclodecadiene derivative. In the absence of a methyl group on C6, the cycloreversion leads to a radical cation complex between 1-methylenecyclopent-2-ene and cyclopentene (12(.+)) which appears to revert to 3 on back electron transfer. The intermediate radical cations 5(.+), 8(.+), and 12(.+) have been identified and characterized by UV/Vis and IR spectra in Ar matrices. The mechanism of their formation is elucidated by quantum chemical calculations.
Stichworte
cycloreversion; photoinduced electron transfer; quantum chemical calculations; radical ions; matrix isolation
Erscheinungsjahr
2006
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
12
Ausgabe
17
Seite(n)
4559-4567
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/1598924

Zitieren

Grota J, Mattay J, Piech K, Bally T. Oxidative rearrangements of tricyclic vinylcyclobutane derivatives. CHEMISTRY-A EUROPEAN JOURNAL. 2006;12(17):4559-4567.
Grota, J., Mattay, J., Piech, K., & Bally, T. (2006). Oxidative rearrangements of tricyclic vinylcyclobutane derivatives. CHEMISTRY-A EUROPEAN JOURNAL, 12(17), 4559-4567. https://doi.org/10.1002/chem.200501338
Grota, J, Mattay, Jochen, Piech, K, and Bally, T. 2006. “Oxidative rearrangements of tricyclic vinylcyclobutane derivatives”. CHEMISTRY-A EUROPEAN JOURNAL 12 (17): 4559-4567.
Grota, J., Mattay, J., Piech, K., and Bally, T. (2006). Oxidative rearrangements of tricyclic vinylcyclobutane derivatives. CHEMISTRY-A EUROPEAN JOURNAL 12, 4559-4567.
Grota, J., et al., 2006. Oxidative rearrangements of tricyclic vinylcyclobutane derivatives. CHEMISTRY-A EUROPEAN JOURNAL, 12(17), p 4559-4567.
J. Grota, et al., “Oxidative rearrangements of tricyclic vinylcyclobutane derivatives”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 12, 2006, pp. 4559-4567.
Grota, J., Mattay, J., Piech, K., Bally, T.: Oxidative rearrangements of tricyclic vinylcyclobutane derivatives. CHEMISTRY-A EUROPEAN JOURNAL. 12, 4559-4567 (2006).
Grota, J, Mattay, Jochen, Piech, K, and Bally, T. “Oxidative rearrangements of tricyclic vinylcyclobutane derivatives”. CHEMISTRY-A EUROPEAN JOURNAL 12.17 (2006): 4559-4567.

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35 References

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Schmittel, Angew. Chem. 109(), 1997

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 36(), 1997

Schmittel, 2001

Bauld, Adv. Electron Transfer Chem. 2(), 1992

Bauld, Acc. Chem. Res. 20(), 1987

Dinnocenzo, J. Am. Chem. Soc. 110(), 1988

Dinnocenzo, Tetrahedron Lett. 36(), 1995

Herbertz, J. Am. Chem. Soc. 120(), 1998

Gassmann, Chemtracts: Org. Chem. 2(), 1989
Thermal [1,3] carbon sigmatropic rearrangements of vinylcyclobutanes.
Leber PA, Baldwin JE., Acc. Chem. Res. 35(5), 2002
PMID: 12020165

Bauld, J. Comput. Chem. 7(), 1990

Pabon, J. Am. Chem. Soc. 106(), 1984

Mattay, Chem. Ber. 121(), 1988

Mattay, Angew. Chem. 99(), 1987

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 26(), 1987

Arnold, J. Am. Chem. Soc. 111(), 1989

Arnold, Can. J. Chem. 72(), 1994

Roth, Acta Chim. Scand. 51(), 1997

Zhou, Tetrahedron Lett. 37(), 1996

Haselbach, Helv. Chim. Acta 62(), 1979

Jungwirth, J. Am. Chem. Soc. 115(), 1993

Zhu, J. Chem. Soc. Perkin Trans. 2 (), 1998

Schroeter, Chem. Eur. J. 6(), 2000

Bally, Chem. Eur. J. 6(), 2000

Bally, Chem. Eur. J. 6(), 2000

Grota, Synthesis (), 2005

Becke, J. Chem. Phys. 97(), 1992
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.
Lee C, Yang W, Parr RG., Phys. Rev., B Condens. Matter 37(2), 1988
PMID: 9944570

AUTHOR UNKNOWN, 0

Casida, 1995

Stratmann, J. Chem. Phys. 109(), 1998

Jungwirth, J. Am. Chem. Soc. 115(), 1993

AUTHOR UNKNOWN, 0
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