Cyclopropane-shift type reaction of diaryl(2- halogenocyclopropyl)methanols promoted by Lewis acids

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5937-5942

  Wakasugi, Kazunori ^a   Nishii, Yoshinori ^b   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE; METHANOL DERIVATIVE;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034729937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00979-5     Document Type: Article

References (19)

1. (a) Houben-Weyl Methods of Organic Chemistry, 4th ed.; Georg Thieme: Stuttgart, 1997; Vol. E17.
2. (b) Patai, S.; Rappoport, S. Z., Eds. The Chemistry of the Cyclopropyl Group; Wiley, London, 1987.
3. (c) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
4. (d) Hiyama, T.; Tsukanaka, M.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 3713.
5. (e) Tanabe, Y.; Nishii, Y. J. Synth. Org. Chem. Jpn. 1999, 57, 170. A recent work: Nishii, Y.; Yoshida, T.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 7195.
6. (e) Tanabe, Y.; Nishii, Y. J. Synth. Org. Chem. Jpn. 1999, 57, 170. A recent work: Nishii, Y.; Yoshida, T.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 7195.
7. (a) Fujita, T.; Ohtsuka, T.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1982, 23, 4091.
8. (b) Hayasaka, K.; Ohtsuka, T.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1985, 26, 873. Related cyclopropane formation was reported: Nagasawa, T.; Handa, Y.; Onoguchi, T.; Suzuki, K. Bull. Chem. Soc. Jpn. 1996, 69, 31.
9. (b) Hayasaka, K.; Ohtsuka, T.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1985, 26, 873. Related cyclopropane formation was reported: Nagasawa, T.; Handa, Y.; Onoguchi, T.; Suzuki, K. Bull. Chem. Soc. Jpn. 1996, 69, 31.
10. Tanabe, Y.; Wakimura, K.; Nishii, Y. Tetrahedron Lett. 1996, 37, 1837. Tanabe, Y.; Nishii, Y.; Wakimura, K. Chem. Lett. 1994, 1757.
11. Tanabe, Y.; Wakimura, K.; Nishii, Y. Tetrahedron Lett. 1996, 37, 1837. Tanabe, Y.; Nishii, Y.; Wakimura, K. Chem. Lett. 1994, 1757.
12. Nishii, Y.; Tanabe, Y.; Wakasugi, K. Synlett 1998, 67.
13. -1 3578, 3057, 1445, 1005, 770, 702, 644.
14. 2 using hexane to give the products 3-1 (R=H; 11 mg, 14%) and 5-1 (R=H; 66 mg, 71%).
15. -1 3061, 1445, 1238, 947, 779, 758, 698.
16. -1 1443, 980, 910, 833, 764, 702.
17. 1e This fact coincides with the reaction of 9a.
18. +). Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Patai, S.; Rappoport, Z., Eds.; Wiley: London, 1987; p. 1223.
19. We propose two mechanistic speculations. One is that bond C not of 2a-1 but of 2b-1 is located in a transannular position toward the leaving OH group and bond C of 2b-1 is longer than bonds A and B; therefore, this bond C is weakened and so inclined to cleave. The other is that cationic intermediate 11 after the cyclopropane-shift is significantly stable compared with normal open chain intermediate 12. These are supported by calculations [SPARTAN version 5.0 (Wavefunction, Inc., Irvine, CA), semiempirical, AM1].