Nature of a Trimethylenemethane-Palladium Complex

Journal of the American Chemical Society

Volumn 102, Issue 20, 1980, Pages 6359-6361

  Trost, Barry M ^a   Chan, Dominic M T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000476567     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00540a041     Document Type: Letter

References (12)

1. For some recent studies, see: Platz, M. S.; Berson, J. A. J. Am. Chem. Soc. 1980, 102, 2358. Duncan, C. D.; Corwin, L. R.; Davis, J. H.; Berson, J. A. Biomedical Sciences Research Fellow. 1980, 102, 2350, and references cited therein. For a review, see: Berson, J. A. Acc. Chem. Res. 1978, 11, 446.
2. Ehrlich, K.; Emerson, G. F. J. Am. Chem. Soc. 1972, 94, 2464. Churchill, M. R.; Gold, K. Inorg. Chem. 1969, 8, 401, Almenningen, A.; Haaland, A.; Wahl, K. Acta Chem. Scand. 1969, 23, 1145.
3. Noyori, R.; Yamakawa, M.; Takaya, H. Tetrahedron Lett. 1978, 4823.
4. Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1979, 101, 6429, 6423.
5. All compounds have been characterized by spectral means. New compounds have satisfactory elemental composition.
6. Cf.: Binger, P.; Schuchardt, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 249. Binger, P.; Cetinkaya, M.; Doyle, M. J.; Germer, A.; Schuchardt, U. Fundam. Res. Homogeneous Catal., Proc. Int. Workshop 1979, 3, 271. Balavoine, G.; Eskenazi, C.; Guillemot, M. J. Chem. Soc., Chem. Commun. 1979, 1109.
7. These calculations were performed by Fenske, R. F.; Gordon, D. of this department. Cf.: Fenske, R. F. Prog. Inorg. Chem. 1976, 21, 179.
8. Prepared by reduction of ethyl 2-(trimethylsilyl) methylacrylate with LAD followed by acetylation. The acrylate was prepared from ethyl 3-(tri-methylsilyl) propanoate (Sommers, L. H.; Marans, N. S. J. Am. Chem. Soc. 1950, 72, 1935) by
9. LDA/THF/-78 °C then (HCHO)., (ii) CH3SO2Cl (C2H5)3N/ether/0 °C, and (iii) DBU/ether/room temperature. For an alternative preparation, see: Hosomi, A.; Hashimoto, H.; Sakurai, H. Tetrahedron Lett. 1980, 951.
10. Extrapolated from the data of Bordwell: (a) Bordwell, F. G.; Bares, J. E.; Bartmess, J. E.; Drucker, G. E.; Gerhold, J.; McCollum, G. J.; Van Der Puy, M.; Vanier, N. R.; Mathwes, W. S. J. Org. Chem. 1977, 42, 326.
11. Bordwell, F. G.; Cornforth, F. J. J. Org. Chem. 1978, 43, 1763.
12. However, reaction of methylenecyclopropanes and olefins catalyzed by palladium is reported to go through TMM complexes (see ref 6). Unfortunately, the available data does not distinguish between a direct cooligomerization reaction (cf. ref 3 and Noyori, R.; Ishigami, T.; Hayashi, N.; Takaya, H. J. Am. Chem. Soc. 1973, 95, 1674) and reaction through TMM