Synthesis and structure of seven-membered metallacyclic alkynes

Organometallics

Volumn 24, Issue 5, 2005, Pages 791-793

  Suzuki, Noriyuki ^a   Aihara, Naoto ^b   Iwasaki, Masakazu ^b   Saburi, Masahiko ^b   Chihara, Teiji ^a  

^a RIKEN   (Japan)

^b SAITAMA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROLYSIS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS; X RAY DIFFRACTION; ZIRCONIUM COMPOUNDS;

CRYSTAL DATA; LIGANDS; METALLCYCLIC STRUCTURE; REACTION MIXTURES;

ORGANOMETALLICS;

EID: 14844283744     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0492449     Document Type: Article

References (38)

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10. There has been discussion of the structures of these compounds; see: (a) Jemmis, E. D.; Phukan, A. K.; Jiao, H.; Rosenthal, U. Organometallics 2003, 22, 4958-4965. (b) Jemmis, E. D.; Phukan, A. K.; Giju, K. T. Organometallics 2002, 21, 2254-2261. (c) Lam, K. C.; Lin, Z. Organometallics 2003, 22, 3466-3470. (d) Rosenthal, U. Angew. Chem., Int. Ed. 2004, 43, 3882-3887.
11. There has been discussion of the structures of these compounds; see: (a) Jemmis, E. D.; Phukan, A. K.; Jiao, H.; Rosenthal, U. Organometallics 2003, 22, 4958-4965. (b) Jemmis, E. D.; Phukan, A. K.; Giju, K. T. Organometallics 2002, 21, 2254-2261. (c) Lam, K. C.; Lin, Z. Organometallics 2003, 22, 3466-3470. (d) Rosenthal, U. Angew. Chem., Int. Ed. 2004, 43, 3882-3887.
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15. 1-Thiacyclohept-4-yne 1,1-dioxide: (a) Bartsch, H.-H.; Colberg, H.; Krebs, A. Z. Kristallogr. 1981, 156, 10-12. 1,2,3,4,5-Pentasilacylohept-6-yne: (b) Ando, W.; Nakayama, N.; Kabe, Y.; Shimizu, T. Tetrahedron Lett. 1990, 31, 3597-3598.
16. The structure of 1-argenta-2,7-dithacyclohept-4-yne, which contains Ag-S dative bonds, has been reported. Gleiter, R.; Rockel, H.; Nuber, B. Chem. Ber. 1996, 129, 581-584.
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20. See also: (c) Bredeau, S.; Delmas, G.; Pirio, N.; Richard, P.; Donnadieu, B.; Meunier, P. Organometallics 2000, 19, 4463-4467.
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27. 2a from the spectra of the mixture. Attempts to isolate 3 by recrystallization have been unsuccessful.
28. 2Zr(alkyne) complexes, see: (a) Buchwald, S. L.; Lum, R. T. J. Am. Chem. Soc. 1986, 108, 7441-7442. (b) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (c) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. (d) Wagenen, B. C. V.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. See also ref 11.
29. 2Zr(alkyne) complexes, see: (a) Buchwald, S. L.; Lum, R. T. J. Am. Chem. Soc. 1986, 108, 7441-7442. (b) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (c) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. (d) Wagenen, B. C. V.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. See also ref 11.
30. 2Zr(alkyne) complexes, see: (a) Buchwald, S. L.; Lum, R. T. J. Am. Chem. Soc. 1986, 108, 7441-7442. (b) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (c) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. (d) Wagenen, B. C. V.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. See also ref 11.
31. 2Zr(alkyne) complexes, see: (a) Buchwald, S. L.; Lum, R. T. J. Am. Chem. Soc. 1986, 108, 7441-7442. (b) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (c) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. (d) Wagenen, B. C. V.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. See also ref 11.
32. w = 0.135, GOF = 1.61.
33. 2O (1 mL) was added at room temperature. After it was stirred for 3 min, the mixture was extracted with diethyl ether (10 mL × 3). The organic layers were combined and dried over magnesium sulfate. The solution was filtered, and the solvent was removed in vacuo. The yellow oily residue was dissolved in hexane, and purification by column chromatography using silica gel (deactivated with 10 v/v % of water) and hexane as an eluent gave 105.8 mg of pure 8 as a colorless liquid in 65% yield based on 7. Hydrolysis with aqueous HCl resulted in higher yield (97% by GC), although it caused desilylation of the product during the purification.
34. Burlakov, V. V.; Ohff, A.; Lefeber, C.; Tillack, A.; Baumann, W.; Kempe, R.; Rosenthal, U. Chem. Ber. 1995, 128, 967-971.
35. Resonance structures between α-vinylzirconacyclopentanes and seven-membered rings have been proposed. For example: (a) Nakamura, A. J. Organomet. Chem. 1990, 400, 36-48 and references therein. (b) Erker, G.; Engel, K.; Dorf, U.; Atwood, J. L.; Hunter, W. E. Angew. Chem., Int. Ed. Engl. 1982, 21, 914-915.
36. Resonance structures between α-vinylzirconacyclopentanes and seven-membered rings have been proposed. For example: (a) Nakamura, A. J. Organomet. Chem. 1990, 400, 36-48 and references therein. (b) Erker, G.; Engel, K.; Dorf, U.; Atwood, J. L.; Hunter, W. E. Angew. Chem., Int. Ed. Engl. 1982, 21, 914-915.
37. (a) Blosser, P. W.; Gallucci, J. C.; Wojcicki, A. J. Am. Chem. Soc. 1993, 115, 2994-2995.
38. See also: (b) Binger, P.; Langhauser, F.; Gabor, B.; Mynott, R.; Herrmann, A. T.; Krüger, C. J. Chem. Soc., Chem. Commun. 1992, 505-506.