Journal of Photoscience

Korean Society of Photoscience (한국광과학회)
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The Link Between Stereoselectivity and Spin Selectivity in Intermolecular and Intramolecular Photochemical Reactions

  • Griesbeck, Axel G. (University of Cologen, Institute of Organic Chemistry)
  • Published : 2003.04.01
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Abstract

How stereo selectivity in singlet and triplet photocycloaddition and photocyclization reactions, respectively, is linked to spin selectivity and how this link affects our understanding of photochemical reaction mechanisms, is described in this review. As illustrative examples, the Paterno-Buchi reaction and the Norrish-Yang cyclization are described with emphasis on triplet biradical structure and dynamics.

Keywords

References

  1. Pure Appl. Chem. v.72 Recent advances in spin chemistry Buchachenko,A.L.
  2. Organic Photochemistry and Photobiology. CRC handbook Oxetane formation: Intermolecular Additions; Oxetane formation: Stereocontrol Griesbeck,A.G.;W.M.Horspool(ed.);P.S.Song(ed.)
  3. Organic Photochemistry and Photobiology. CRC handbook Norrish type Ⅱ photoelimination of ketones: Cleavage of 1,4-biradicals formed by γ-hydrogen abstraction; Norrish type Ⅱ processes of ketones: Influence of evnironment Wagner,P.J.;W.M.Horspool(ed.);P.S.Song(ed.)
  4. J. Am. Chem. Soc. v.112 Photo-cycloaddition of benzaldehyde to cyclic olefins: Electronic control of endo stereoselectivity Griesbeck,A.G.;S.Stadtmuller
  5. Acc. Chem. Res. v.27 Intersystem crossing in triplet 1,4-biradicals: Conformational memory effects on the stereoselectivity of photocycloaddition reactions Griesbeck,A.G.;H.Mauder;S.Stadtmuller
  6. Tetrahedron Lett. v.37 Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate Buhr,S.;A.G.Griesbeck;J.Lex;J.Mattay;J.Schroer
  7. J. Org. Chem. v.62 Rapid regio- and diastereo-selective Paterno-Buchi reaction of alkyl phenylglyoxylates Hu,S.;D.C.Neckers
  8. Chem. Rev. v.89 Time-resolved studies of biradical reactions in solution Johnston,L.J.;J.C.Scaiano
  9. Angew. Chem. Int. Ed. Engl. v.11 Electronic properties of diradicals Salem,L.;C.Rowland
  10. J. Am. Chem. Soc. v.109 Spin-orbit coupling in biradicals. Abinitio MCSCF calculations on trimethylene and the methyl-methyl radical pair Carlacci,L.;C.Doubleday,Jr.;T.R.Furlani;H.F.King;J.W.McIver
  11. J. Am. Chem. Soc. v.107 Picosecond dynamics of the Paterno-Buechi reaction Freilich,S.C.;K.S.Peters
  12. Pure Appl. Chem. v.69 Theoretical models for the selectivity of organic singlet and triplet photoreactions Klessinger,M.
  13. Chem. Ber. v.124 Photocycloadditionen mit α- und β-Naphthaldehyd: Vollstandige Umkehr der Diastereoselek-tivitat als Konsequenz unterschiedlich konfigurierter elektronischer Zustande Griesbeck,A.G.;H.Mauder;K.Peters;E.M.Peters;H. G. von Schnering
  14. J. Am. Chem. Soc. v.113 Electronic control of stereoselectivity in photocycloaddition reactions: Part 4. Effects of methyl substituents at the donor olefin Griesbeck,A.G.;S.Stadtmuller
  15. Bull. Korean Chem. Soc. v.19 Diastereoselective Routes in the Paterno-Buchi reactions of cyclic enol ortho ester with aldehydes Park,S.K.;S.J.Lee;K.Baek;C.M.Yu
  16. J. Chem. Soc., Perkin Trans. v.1 Regioselective formation of 2-alkoxyoxetanes in the photoreaction of aromatic carbonyl compounds with β,β-dimethyl ketene silyl acetals: Notable solvent and silyl group effects Abe,M.;Y.Shirodai;M.Nojima
  17. J. Org. Chem. v.63 Stereoselectivity of triplet photocycloadditions: Diene-carbonyl reactions and solvent effects Griesbeck,A.G.;S.Buhr;M.Fiege;H.Schmickler;J.Lex
  18. J. Am. Chem. Soc. v.118 Photoinduced electron transfer reactions of aryl olefins. 2. Cis-trans isomerization and cycloadduct formation in anethole-fumaronitrile systems in polar solvents Goez,M.;G.Eckert
  19. Science v.227 [2+2] Photocycloadditions in the synthesis of chiral molecules Schreiber,S.L.
  20. Chem. Commun. Oxazole-carbonyl photocycloadditions: selectivity pattern and synthetic route to erythro α-amino, β-hydroxy ketones Griesbeck,A.G.;M.Fiege;J.Lex
  21. J. Am. Chem. Soc. v.123 Conformational analysis of singlet-triplet state mixing in Paterno-Buchi diradicals Kutateladze,A.G.
  22. Org. Lett. v.2 Spin-directed stereoselectivity of carbonyl-alkene photocycloadditions Griesbeck,A.G.;M.Fiege;S.Bondock;M.S.Gudipati
  23. J. Am. Chem. Soc. v.116 An MC-SCF study of the (photochemical) Paterno-Buchi reaction Palmer,I.J.;I.N.Ragazos;F.Bernardi;M.Olivucci;M.A.Robb
  24. Angew. Chem. Int. Ed. v.40 Temperature and viscosity dependence of the spin-directed stereoselectivity of the carbonyl-alkene photocycloaddition Griesbeck,A.G.;S.Bondock;M.S.Gudipati
  25. J. Am. Chem. Soc. v.80 Photochemical reactions of ketones in solution Yang,N.C.;D.H.Yang
  26. Tetrahedron v.55 The Norrish Ⅱ reaction in the crystalline state: Toward a better understanding of the geometrical requirements for γ-hydrogen atom abstraction Ihmels,H.;J.R.Scheffer
  27. J. Am. Chem. Soc. v.124 Stereoselective synthesis of 2-aminocyclobutanols via photocyclization of α-amido alkylaryl ketones: Mechanistic implications for the Norrish/Yang reaction Griesbeck,A.G.;H.Heckroth
  28. Tetrahedron v.38 Does intersystem crossing in triplet biradicals generat singlets with conformational memory? Scaiano,J.C.