Enhanced nucleophilicity of ambiphilic silylene and silylenoid bearing 8-(dimethylamino)-1-naphthyl group

Journal of Organometallic Chemistry

Volumn 600, Issue 1-2, 2000, Pages 118-123

  Tamao, Kohei ^a   Asahara, Masahiro ^a   Saeki, Tomoyuki ^a   Toshimitsu, Akio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

1,2 Disilaace naphthene; 1 Silaphenalene; 8 (Dimethylamino) 1 naphthyl group; Base coordinated silylene; Silaylide; Silicon; Silylene; Silylenoid

Indexed keywords

EID: 0000645550     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00144-3     Document Type: Article

References (53)

1. Apeloig Y. Patai S., Rappoport Z. The Chemistry of Organic Silicon Compounds. 1989;Wiley, Chichester, UK. Ch. 2.
2. Driess M., Grützmacher H. Int. Ed. Engl. Angew. Chem. 35:1996;828.
3. Kira M., Ishida S., Iwamoto T., Kabuto C. J. Am. Chem. Soc. 121:1999;9722. and Refs. cited therein.
4. Recent review Belzner J. Adv. Organomet. Chem. 43:1999;1.
5. Isolatable nucleophilic divalent silicon species Jutzi P., Kanne D., Krüger C. Int. Ed. Engl. Angew. Chem. 25:1986;164.
6. Jutzi P., Hotmann U., Kanne D., Krüger C., Blom R., Gleiter R., Hyla-Krypsin I. Chem. Ber. 122:1989;1629.
7. Karsch H.H., Keller U., Gamper S., Müller G. Int. Ed. Engl. Angew. Chem. 29:1990;295.
8. Denk M., Lennon R., Hayashi R., West R., Belyakov A.V., Verne H.P., Haaland A., Wagner M., Metzler N. J. Am. Chem. Soc. 116:1994;2691.
9. Metzler N., Denk M. Chem. Commun. (Cambridge). 1996;2657.
10. Gehrhus B., Leppert M.F., Heinicke J., Boese R., Bläser D. J. Chem. Soc. Chem. Commun. 1995;1931.
11. Weidenbruch M. Eur. J. Inorg. Chem. 1999;373.
12. Seyferth D., Lim T.F.O. J. Am. Chem. Soc. 100:1978;7074.
13. Reactivity Steele K.P., Weber W.P. J. Am. Chem. Soc. 102:1980;6095.
14. Levin G., Das P.K., Lee C.L. Organometallics. 7:1988;1231.
15. Levin G., Das P.K., Bilgrien G., Lee C.L. Organometallics. 8:1989;1206.
16. Spectroscopy Ando W., Hagiwara K., Sekiguchi A. Organometallics. 6:1987;2270.
17. Ando W., Sekiguchi A., Hagiwara K., Sakakibara A., Yoshida H. Organometallics. 7:1988;558.
18. Gillette G.R., Noren G.H., West R. Organometallics. 6:1987;2617.
19. Gillette G.R., Noren G.H., West R. Organometallics. 8:1989;487.
20. Theoretical study Rahgavachari K., Chandrasekhar J., Gordon M.S., Dykema K.J. J. Am. Chem. Soc. 106:1984;5853.
21. Conlin R.T., Laakso D., Marshall P. Organometallics. 13:1994;838.
22. Apeloig Y., Müller T. J. Am. Chem. Soc. 117:1995;5363.
23. Schoeller W.W., Schneider R. Chem. Ber./Recueil. 130:1997;1013.
24. Isolation Takeda N., Suzuki H., Tokitoh N., Okazaki R. J. Am. Chem. Soc. 119:1997;1456.
25. Corriu R., Lanneau G., Priou C., Soulairol F., Auner N., Probst R., Conlin R., Tan C. J. Organomet. Chem. 466:1994;55.
26. Corriu R.J.P., Chauhan B.P.S., Lanneau G.F. Organometallics. 14:1995;1646.
27. Chauhan B.P.S., Corriu R.J.P., Lanneau G.F., Priou C., Auner N., Handwerker H., Herdtweck E. Organometallics. 14:1995;1657.
28. Belzner J. Auner N., Weis J. Organosilicon Chemistry III: From Molecules to Materials. 1998;58 VCH, Weinheim.
29. Belzner J., Dehnert U., Ihmels H., Hübner M., Müller P., Uson I. Chem. Eur. J. 4:1998;852.
30. Tamao K., Nagata K., Asahara M., Kawachi A., Ito Y., Shiro M. J. Am. Chem. Soc. 117:1995;11592.
31. K. Tamao, M. Asahara, T. Saeki, S.-G. Feng, A. Kawachi, A. Toshimitsu, Chem. Lett., submitted for publication.
32. K. Tamao, M. Asahara, A. Toshimitsu, Chem. Lett., submitted for publication.
33. Tamao K., Tarao Y., Nakagawa Y., Nagata K., Ito Y. Organometallics. 12:1993;1113.
34. Tamao K., Asahara M., Kawachi A. J. Organomet. Chem. 521:1996;325.
35. Tamao K., Asahara M., Sun G.-R., Kawachi A. J. Organomet. Chem. 574:1999;193.
36. Tamao K., Asahara M., Saeki T., Toshimitsu A. Int. Ed. Engl. Angew. Chem. 38:1999;3316.
37. Atwell W.H., Weyenberg D.R. J. Organomet. Chem. 5:1966;594.
38. Atwell W.H., Weyenberg D.R. J. Am. Chem. Soc. 90:1968;3438.
39. Atwell W.H., Weyenberg D.R. Int. Ed. Engl. Angew. Chem. 8:1969;469.
40. Schmeisser M., Ehlers K.-P. Int. Ed. Engl. Angew. Chem. 3:1964;700.
41. It has been known that the reaction of silylene and 1,3-diene first gives the 1,2-addition product, i.e. 2-vinyl-1-silacyclopropane, which rearranges to the silacylopentene framework: Clarke M.P., Davidson I.M.T. J. Chem. Soc. Chem. Commun. 1988;241.
42. Clarke M.P., Davidson I.M.T., Dillon M.P. J. Chem. Soc. Chem. Commun. 1988;1139.
43. An addition - elimination mechanism and an electron-transfer mechanism may be envisioned for the 'nucleophilic substitution' of the ammonium moiety from the naphthyl carbon by the silicon or carbon anionic center 12 or 13, but further study is necessary for clarification of the mechanism.
44. It has been established that silylene adds to an acetylene to give a silacylcopropene ring, but in our case, no such three-membered product was obtained. See Ishikawa M., Kumada M. Adv. Organomet. Chem. 19:1981;51.
45. Ishikawa M., Nakagawa K.-I., Kumada M. J. Organomet. Chem. 190:1980;117.
46. Hojo F., Sekigawa S., Nakayama N., Shimizu T., Ando W. Organometallics. 12:1993;803.
47. Belzner J., Ihmels H. Tetrahedron Lett. 34:1993;6541.
48. Sakamoto K., Tsutsumi S., Sakurai H., Kira M. Bull. Chem. Soc. Jpn. 70:1997;253 We propose this nucleophilic addition mechanism, contrary to the traditional 1,2-addition/rearrangement mechanism for electrophilic silylenes (see Ref. [12]).
49. We have recently reported that pseudo-pentacoordinated monochlorosilicon compounds smoothly undergo the magnesium mediated coupling to form the silicon - silicon bond: Tamao K., Asahara M., Saeki T., Toshimitsu A. Chem. Lett. 1999;335.
50. Tamao K., Kawachi A. Int. Ed. Engl. Angew. Chem. 34:1995;818.
51. Tanaka Y., Hada M., Kawachi A., Tamao K., Nakatsuji H. Organometallics. 17:1998;4573.
52. Boudjouk P., Kiely J.S., Sooriyakumaran R. J. Organomet. Chem. 221:1981;33.
53. Afanasova O.B., Kirillova N.I., Chernyshev E.A., Struchkov Yu.T. J. Organomet. Chem. 536-537:1997;31.