Pyrylium Salts as Photosensitizers in Homogeneous and Heterogeneous Electron‐Transfer Catalysis. – A Comparison with Cyano Arenes

Wiley - Tập 122 Số 5 - Trang 951-958 - 1989
Jochen Mattay1, Martin Vondenhof1, R. Denig2
1Institut für Organische Chemie der Technischen Hochschule Aachen, Prof.-Pirlet-Str. 1, D-5100 Aachen, West Germany
2BASF-Aktiengesellschaft, D-6700 Ludwigshafen, West Germany

Tóm tắt

AbstractTwo new triphenylpyrylium salts, both being fixed to a polymeric backbone, have been synthesized. They a sensitizers for photochemically induced electron‐transfer. reactions, offering the possibility of heterogeneous charge transfer. Their usability in electron‐transfer‐catalyzed dimerizations and mixed cycloadditions of 1,3‐cyclohexadiene and phenyl vinyl ether has been tested in comparison to other common photosensitizers such as 9,10‐dicyanoanthracene and 1,4‐dicyanonaphthalene. In addition, 2,4,6‐triphenylpyrylium tetrafluoroborate was shown to operate as an efficient sensitizer for the dimerization and the photooxygenation of 1,1‐diphenylethene. Diverse selectivities in the products formation indicate different mechanisms and are discussed in view of earlier results reported in the literature.

Từ khóa


Tài liệu tham khảo

Part 23 ofRadical Ions and Photochemical Charge Transfer Phenomena; for part 22 see ref.2.

W. S.Chung N. J.Turro J.Mertes J.Mattay J. Am. Chem. Soc. submitted.

10.1021/bk-1986-0308

10.1021/ja00897a025

D. C.Neckersin ref.3p.107.

10.1021/jo01284a058

10.1002/ange.19870990906

10.1002/anie.198708251

10.1002/nadc.19880360409

Mattay J., 1988, EPA Newslett., 32, 23

Farid S., Chem. Commun., 1973, 677

Mattes S. L., 1983, Organic Photochemistry, 233

10.1002/ange.19870990906

10.1002/anie.198504121

10.1055/s-1981-29405

L.Eberson personal communication:L.Eberson B.Olofsson Acta Chem. Scand. Ser. B in press.

10.1021/ja00238a027

10.1021/ar00142a003

10.1002/prac.19773190617

Kawata H., Tetrahedron Lett., 1986, 4489

10.1002/pol.1965.110030617

Lombard R., Bull. Soc. Chim. Fr., 1958, 1458

10.1021/jo01063a611

10.1002/app.1959.070020619

10.1002/pol.1960.1204514604

10.1002/app.1960.070030908

10.1002/cber.19881211116

10.1021/ja01077a033

10.1002/ange.19860980132

10.1002/anie.198601011

10.1515/znb-1964-0105

10.1021/ar00142a003

10.1021/ja00341a072

Murov S. L., 1973, Handbook of Photochemistry

10.1021/ja01042a004

(32a)J.Mertes J.Mattay W. S.Chung N. J.Turro. – XII. IUPAC Symposium on Photochemistry Bologna (Italy) July 17–22 1988 Proceedings p.625.

(32b) – 10. Vortragstagung der Fachgruppe Photochemie Würzburg (F.R.G.) Nov. 18–20 1987 Proceedings. p.165–167.

10.1021/ja00220a071

10.1021/jo00961a036

10.1016/B978-0-12-290650-3.50020-8

10.1016/B978-0-12-290650-3.50019-1

10.1021/j150642a003

10.1021/ja00353a065

M.Vondenhof Diploma Thesis RWTH Aachen1988.

10.1021/ja00793a060

10.1021/ja00283a034

10.1021/ja00539a018

Moutet J. C., Tetrahedron Lett., 1979, 2389

Gollnick K., Tetrahedron Lett., 1984, 185

Akaba R., J. Chem. Soc., Chem. Comm., 1987, 1262

10.1021/ja00343a061

The preferential formation of27in the dimerization of26catalyzed by2has also been studied byE.Steckhan Bonn (personal communication).

J. P.Schaefer L.Endres Org. Synth.Coll. Vol. V(1973)285.

10.1246/bcsj.41.818

C. F. H.Allen S.Converse Org. Synth.Coll. Vol. I(1941)226.

Berçot P., Bull. Soc. Chim. Fr., 1947, 304

Bradbrook E. F., J. Chem. Soc., 1936, 1739

10.1016/S0040-4020(01)99274-9

Braun D., 1979, Praktikum der makromolekularen organischen Chemie, 551

Thông tin
Thông tin xuất bản

Wiley

Tập 122 Số 5

951-958

Thông tin tác giả