Novel rhodium-catalyzed cyclic carbonylation of 2- phenylethynylbenzoates leading to indeno[1,2-c]isocoumarin

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 4989-4992

  Sugioka, Takashi ^a   Yoneda, Eiji ^a   Onitsuka, Kiyotaka ^a   Zhang, Shi Wei ^a   Takahashi, Shigetoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ESTER; ISOCOUMARIN DERIVATIVE; LACTONE DERIVATIVE; RHODIUM;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; CYCLIZATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; X RAY CRYSTALLOGRAPHY;

EID: 0030861810     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01067-8     Document Type: Article

References (23)

1. See, for example, Wender, I.; Pino, P. Organic Syntheses via Metal Carbonyls, John Wiley & Sons, New York, 1977, Vol. 2.
2. a) Reppe, W.; Vetter, H. Ann., 1953, 121, 582;
3. b) Kang, H. C.; Mauldin, C. H.; Cann, K.; Pettit, R. J. Am. Chem. Soc., 1977, 99, 8323-8325;
4. c) King, A. D.; King, D. B.; Yang, D. B. J. Am. Chem. Soc., 1980, 102, 1028-1032.
5. a) Ungermann, C.; Landis, V.; Moya, S. A.; Walker, H.; Rinker, R. G.; Ford, P. C. J. Am. Chem. Soc., 1979, 101, 5922-5929;
6. b) Bricker, J. C.; Nagel, C. C.; Shore, S. G. J. Am. Chem. Soc., 1982, 104, 1444-1445.
7. a) Laine, R. M. J. Am. Chem. Soc., 1978, 100, 6451-6454;
8. b) Chini, P.; Longoni, G.; Albano, V. Adv. Organomet. Chem., 1976, 14, 285-344;
9. c) Kaneda, K.; Hiraki, M.; Sano, K.; Imanaka, T.; Teranishi, S. J. Mol. Catal., 1980, 9, 227-233.
10. Joh, T.; Doyama, K.; Onitsuka, K.; Shiohara, T.; Takahashi, S. Organometallics, 1991, 10, 2493-2497.
11. Hirao, K.; Morii, N.; Joh, T.; Takahashi, S. Tetrahedron Lett., 1995, 36, 6243-6246.
12. Sugioka, T.; Zhang, S.-W.; Morii, N.; Joh, T.; Takahashi, S. Chem. Lett., 1996, 249-250.
13. 2: C 82.04, H 4.30%; Found: C 82.12, H 4.13%.
14. w) = 0.058(0.048) for 203 parameters against 1540 reflections [I > 3σ(I)] out of 2689 unique reflections corrected for absorption using φ-scan technique and decay, GOF = 3.13. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre. See Information for Authors, Issue No. 1. Selected bond distances (Å) and angles (°): O(1)-C(13) 1.200(3), O(2)-C(13) 1.396(3), O(2)-C(16) 1.371(3), C(14)-C(16) 1.339(4), C(14)-C(15) 1.507(4); O(2)-C(13)-C(2) 117.2(3), C(13)-O(2)-C(16) 119.2(2), O(2)-C(16)-C(14) 124.8(3), C(3)-C(14)-C(16) 120.4(3), C(7)-C(16)-C(14) 112.9(3), C(15)-C(14)-C(16) 108.6(3).
15. The structures of furanones 4a and 5a are as follows: (equation presented)
16. 3 (1.2 ml), 1,4-dioxane (30 ml).
17. a) Mori Y.; Tsuji, J. Tetrahedron, 1972, 28, 29;
18. b) Matsumoto, H.; Nakano, T.; Ohkawa, K.; Nagai, Y. Chem. Lett, 1978, 363-366;
19. c) Molander, G. A.; McKie, J. A. J. Org. Chem., 1993, 58, 7216-7227.
20. a) Yamamoto, T.; Ishizu, J.; Kohara, T.; Komiya, S.; Yamamoto, A. J. Am. Chem. Soc., 1980, 102, 3758-3764;
21. b) Hayashi, Y.; Yamamoto, T.; Yamamoto, A.; Komiya, S.; Kushi, Y. J. Am. Chem. Soc., 1986, 108, 385-391;
22. c) Yamamoto, T.; Miyashita, S.; Naito, Y.; Komiya, S.; Ito, T.; Yamamoto, A. Organometallics, 1982, 1, 808-812.
23. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis, 1980, 627-630.