Unexpected reaction of a dimethylzinc-generated THF radical with aldehydes

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 795-797

  Yamamoto, Yasutomo ^a   Yamada, Ken Ichi ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; DIMETHYLZINC; TETRAHYDROFURAN; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; OXYGENATION;

EID: 0347418216     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.037     Document Type: Article

References (28)

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6. (a) For recent impressive α-alkoxy radical reactions, see: Fernández M., Alonso R. Org. Lett. 5:2003;2461-2464 (b) Tsujimoto S., Sakaguchi S., Ishii Y. Tetrahedron Lett. 44:2003;5601-5604 (c) Hirano K., Sakaguchi S., Ishii Y. Tetrahedron Lett. 43:2002;3617-3620 (d) Mosca R., Fagnoni M., Mella M., Albini A. Tetrahedron. 57:2001;10319-10328 (e) Torrente S., Alonso R. Org. Lett. 3:2001;1985-1987 (f) Kim S., Kim N., Chung W.-J., Cho C.H. Synlett. 2001;937-940.
7. (a) For recent impressive α-alkoxy radical reactions, see: Fernández M., Alonso R. Org. Lett. 5:2003;2461-2464 (b) Tsujimoto S., Sakaguchi S., Ishii Y. Tetrahedron Lett. 44:2003;5601-5604 (c) Hirano K., Sakaguchi S., Ishii Y. Tetrahedron Lett. 43:2002;3617-3620 (d) Mosca R., Fagnoni M., Mella M., Albini A. Tetrahedron. 57:2001;10319-10328 (e) Torrente S., Alonso R. Org. Lett. 3:2001;1985-1987 (f) Kim S., Kim N., Chung W.-J., Cho C.H. Synlett. 2001;937-940.
8. (a) For recent impressive α-alkoxy radical reactions, see: Fernández M., Alonso R. Org. Lett. 5:2003;2461-2464 (b) Tsujimoto S., Sakaguchi S., Ishii Y. Tetrahedron Lett. 44:2003;5601-5604 (c) Hirano K., Sakaguchi S., Ishii Y. Tetrahedron Lett. 43:2002;3617-3620 (d) Mosca R., Fagnoni M., Mella M., Albini A. Tetrahedron. 57:2001;10319-10328 (e) Torrente S., Alonso R. Org. Lett. 3:2001;1985-1987 (f) Kim S., Kim N., Chung W.-J., Cho C.H. Synlett. 2001;937-940.
9. (a) For recent impressive α-alkoxy radical reactions, see: Fernández M., Alonso R. Org. Lett. 5:2003;2461-2464 (b) Tsujimoto S., Sakaguchi S., Ishii Y. Tetrahedron Lett. 44:2003;5601-5604 (c) Hirano K., Sakaguchi S., Ishii Y. Tetrahedron Lett. 43:2002;3617-3620 (d) Mosca R., Fagnoni M., Mella M., Albini A. Tetrahedron. 57:2001;10319-10328 (e) Torrente S., Alonso R. Org. Lett. 3:2001;1985-1987 (f) Kim S., Kim N., Chung W.-J., Cho C.H. Synlett. 2001;937-940.
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12. These compounds gave satisfactory spectroscopic and analytical data. The compounds 7a and 8 were known compound. 7a : Jedlinski Z., Kowalczuk M., Kurcok P., Grzegorzek M., Ermel J. J. Org. Chem. 52:1987;4601-4602. 8 : Enholm E.J., Schreier J.A. J. Heterocyclic Chem. 32:1995;109-111.
13. These compounds gave satisfactory spectroscopic and analytical data. The compounds 7a and 8 were known compound. 7a : Jedlinski Z., Kowalczuk M., Kurcok P., Grzegorzek M., Ermel J. J. Org. Chem. 52:1987;4601-4602. 8 : Enholm E.J., Schreier J.A. J. Heterocyclic Chem. 32:1995;109-111.
14. 1H NMR of the crude product.
15. Diorganozinc-oxygen derived complex has been isolated as a possible radical precursor. Lewinski J., Marciniak W., Lipkowski J., Justyniak I. J. Am. Chem. Soc. 125:2003;12698-12699.
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19. (d) Kim, S.; Yoon, J.-Y. In Radicals in Organic Synthesis; Renaud, P., Sibi, M.P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, Chapter 1.1.3, pp. 11-12.
20. (a) For the addition to acylsilanes, see: Huang C.-H., Chang S.-Y., Wang N.-S., Tsai Y.-M. J. Org. Chem. 66:2001;8983-8991. and references cited therein
21. (b) For the addition to thioesters, selenoesters, acylgermanes, and acylphosphonate, see: Kim S., Cho C.H., Lim C.J. J. Am. Chem. Soc. 125:2003;9574-9575. and references cited therein.
22. (a) For tributyltin hydride-mediated pinacol coupling, see: Hays D.S., Fu G.C. J. Org. Chem. 63:1998;6375-6381
23. (b) Hays D.S., Fu G.C. J. Am. Chem. Soc. 117:1995;7283-7284.
24. For intramolecular cyclization of α-stannyl radical to a formyl group, see: Chang S.-Y., Shao Y.-F., Chu S.-F., Fan G.-T., Tsai Y.-M. Org. Lett. 1:1999;945-948.
25. (a) For intramolecular radical cyclization to a formyl group with excess silanes, see: Batey R.A., MacKay D.B. Tetrahedron Lett. 39:1998;7267-7270
26. (b) With excess organophosphorous compound, see: Kim S., Oh D.H. Synlett. 1998;525-527.
27. THF α-adduct 5 was obtained rather than β-adduct 6 by using triethylborane-air as an initiator, probably due to the fast reaction of 14 with triethylborane. See Refs.[3a,3b,3c].
28. Bond dissociation energies of HOO-H and HO-H have been reported to be 87.2 and 119 kcal/mol, respectively. MacMillen D.F., Golden D.M. Ann. Rev. Phys. Chem. 33:1982;493-532.