Comparing α-carbanion-stabilizing ability of substituents using the Brook rearrangement

Tetrahedron Letters

Volumn 39, Issue 29, 1998, Pages 5243-5246

  Takeda, Kei ^a   Ubayama, Haruka ^a   Sano, Ayako ^a   Yoshii, Eiichi ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Carbanions; Rearrangements; Silicon and Compounds; Substituent effects

Indexed keywords

FUNCTIONAL GROUP;

ARTICLE; MOLECULAR DYNAMICS; MOLECULAR STABILITY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032537687     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01032-6     Document Type: Article

References (18)

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2. (b) Takeda K, Sakurama K, Yoshii E. Tetrahedron Lett. 1997;38:3257-3260.
3. [2] Takeda K, Takeda M, Nakajima A, Yoshii E. J. Am. Chem. Soc. 1995;117:6400-6401.
4. (b) Takeda K, Nakajima A, Yoshii E. Synlett; 1996:753-754.
5. (c) Takeda K, Nakajima A, Takeda M, Okamoto Y, Sato T, Yoshii E, Koizumi T, Shiro M. J. Am. Chem. Soc. 1998;120:in press.
6. [3] For the silicon atom, see : (a) Bassindale AR, Taylor PG. Activating and directive effects of silicon. In: Patai S, Rappoport Z, editors. The Chemistry of Organic Silicon Compounds. New York: John Wiley & Sons, 1989:893-963.
7. (b) Wetzl DM, Brauman JI. J. Am. Chem. Soc. 1988;110:8333-8336 and references cited therein.
8. For the sulfur atom, see: (c) Wiberg KB, Catejon H. J. Am. Chem. Soc. 1994;116:10489-10497 and references cited therein.
9. (d) Bernasconi CF, Kittredge KW. J. Org. Chem. 1998;63:1944-1953.
10. Also, see: (e) Römer B, Gatev GG, Ahong M, Brauman JI. J. Am. Chem. Soc. 1988;120:2919-2924.
11. [4] For pKa values for many types of acids, including one containing α-heteroatoms, see: Bordwell FG. Acc. Chem. Res. 1988;21:456-463.
12. [5] (a) For reviews of the Brook rearrangement, see: (a) Brook AG, Bassindale AR. Molecular rearrangements of organosilicon compounds. In: de Mayo P, editor. Rearrangements in Ground and Excited States. New York: Academic Press, 1980;Vol.2:149-221.
13. (b) Brook AG. Acc. Chem. Res. 1974;7:77-84.
14. [6] Picard JP, Calas R, Dunogues J, Duffaut N, Gerval J, Lapouyade P. J. Org. Chem. 1979;44:420-424.
15. [7] Reaction of 6 with ketone enolates afforded 1,2-cyclopropanediol derivative ii by way of Brook rearrangement of the initial 1,2-adduct i and subsequent internal attack on the β-carbonyl group. No 1,2-addition product was obtained, which could be explainable by acceleration of the Brook rearangement by the more electrophilic ketone carbonyl group relative to the ester carbonyl group, see: Takeda K, Nakatani J, Nakamura H, Sako K, Yoshii E, Yamaguchi K. Synlett; 1993:841-843. (Equation Presented)
16. [8] Nowick JS, Danheiser RL. J. Org. Chem. 1989;54:2798-2802.
17. [9] Reich HJ, Kelly MJ, Olson RE, Holtan RC. Tetrahedron 1983;39:949-960.
18. [10] Brook and coworkers reported the rate of amine base-catalyzed rearrangement of a wide variety of α-silylcarbinols. Brook AG, LeGrow GE, MacRae DM. Can. J. Chem. 1967;45:239-253.