Electron Transfer Induced Deprotection of Benzyl Substituted 1,3-Dithianes with Iron(III)phenanthroline Complexes

Synlett

Volumn 1996, Issue 4, 1996, Pages 315-316

  Schmittel, Michael ^a   Levis, Michael ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001874030     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5412     Document Type: Article

References (18)

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2. (a) Seebach, D. Synthesis 1969, 17;
3. (b) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357.
4. +/iodine: Nishide, K.; Yokota, K.; Nakamura, D.; Sumiya, T.; Node, M.; Ueda, M.; Fuji, K. Tetrahedron Lett. 1993, 34, 3425.
5. Platen, M.; Steckhan, E. Chem. Ber. 1984, 117, 1679.
6. (a) Kamata, M.; Kato, Y.; Hasegawa, E. Tetrahedron Lett. 1991, 32, 4349;
7. (b) Kamata, M.; Sato, M.; Hasegawa, E. Tetrahedron Lett. 1992, 33, 5085;
8. (c) Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821.
9. (a) Schmittel, M.; Abufarag, A.; Luche, O.; Levis, M. Angew. Chem. 1990, 102, 1174; Angew. Chem. Int. Ed. Engl. 1990, 29, 1144;
10. (a) Schmittel, M.; Abufarag, A.; Luche, O.; Levis, M. Angew. Chem. 1990, 102, 1174; Angew. Chem. Int. Ed. Engl. 1990, 29, 1144;
11. (b) Schmittel, M.; Levis, M. Chem. Lett. 1994, 1935.
12. 2+ salts led to decomposition of the ketone during workup (using either distillation or chromatography).
13. 1/2 = 0.39 V vs. SCE).
14. Cristau, H.-J.; Chabaud, B.; Labaudinière, R.; Christol, H. Syn. Commun. 1981, 11, 423.
15. Wong, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 5593.
16. 3+ did not improve conversion.
17. 3) calcd. 284.1424, found 284.1415.
18. The analysis of the recovered iron(II)phenanthroline revealed that a small part of it was substituted by organosulfur groups. Consequently, reuse of the recovered iron(II) complex is only feasible after purification.