New construction of ortho ring-alkylated phenols via generation and reaction of assorted o-quinone methides [8]

Journal of the American Chemical Society

Volumn 122, Issue 27, 2000, Pages 6502-6503

  Van De Water, Ryan W ^a   Magdziak, Derek J ^a   Chau, Jennifer N ^a   Pettus, Thomas R R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYLPHENOL; KETONE; MAGNESIUM; ORGANOLITHIUM COMPOUND; QUINONE DERIVATIVE;

CHEMICAL BOND; HALOGENATION; LETTER; REACTION ANALYSIS; REACTION TIME; REDUCTION; SYNTHESIS; TEMPERATURE;

EID: 0034641283     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994209s     Document Type: Letter

References (17)

1. For work regarding Claisen rearrangement, see: Rhoads, S. J. Organic Reactions, 1974; Vol. 22, p 1. For work regarding the Fries rearrangement see, Martin R. Org. Prepr. Proced. Int. 1992, 24, 369-435.
2. For work regarding Claisen rearrangement, see: Rhoads, S. J. Organic Reactions, 1974; Vol. 22, p 1. For work regarding the Fries rearrangement see, Martin R. Org. Prepr. Proced. Int. 1992, 24, 369-435.
3. Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365-368.
4. Snieckus, V. Chem. Rev. 1990, 90, 879-933.
5. Mitchell, R. H.; Lai, Y.-H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733-4735.
6. Oxidative insertion with an electron-rich aryl halide is exceedingly difficult. Knochel, P.; Majid, T. Tetrahedron Lett. 1990, 31, 4413-4416.
7. McLoughlin, B. J. J. Chem. Soc., Chem. Commun. 1969, 540-541.
8. Mitchell, D.; Doecke, C.; Hay, L. A.; Koenig, T. M.; Wirth, D. D. Tetrahedron Lett. 1995, 36, 5335-5338.
9. Angle, S. R.; Rainier, J. D.; Woytowicz, C. J. Org. Chem. 1997, 62, 5884-5892.
10. o-Quinone methides are of potential use in the alkylation of DNA, see: Pande, P.; Shearer, J.; Yang J.; Greenberg, W. A.; Rokita, S. E. J. Am. Chem. Soc. 1999, 121, 6773-6779. For other o-quinone methide chemistry, see: Taing, M.; Moore, H. J. Org. Chem. 1996, 61, 329-340 and Turnbull, K.; Casnati, G.; Pochini, A.; Terenghi, M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783-3787.
11. o-Quinone methides are of potential use in the alkylation of DNA, see: Pande, P.; Shearer, J.; Yang J.; Greenberg, W. A.; Rokita, S. E. J. Am. Chem. Soc. 1999, 121, 6773-6779. For other o-quinone methide chemistry, see: Taing, M.; Moore, H. J. Org. Chem. 1996, 61, 329-340 and Turnbull, K.; Casnati, G.; Pochini, A.; Terenghi, M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783-3787.
12. o-Quinone methides are of potential use in the alkylation of DNA, see: Pande, P.; Shearer, J.; Yang J.; Greenberg, W. A.; Rokita, S. E. J. Am. Chem. Soc. 1999, 121, 6773-6779. For other o-quinone methide chemistry, see: Taing, M.; Moore, H. J. Org. Chem. 1996, 61, 329-340 and Turnbull, K.; Casnati, G.; Pochini, A.; Terenghi, M.; Ungaro, R. J. Org. Chem. 1983, 48, 3783-3787.
13. (a) Muller, B. Br. Corros. J. 1996, 31, 315-317.
14. (b) Muller, B. Mater. Corros. 1999, 50, 213-218.
15. Johnson, H. A.; Rogers, L. L.; Alkire, M. L.; McCloud, T. G.; McLaughlin, J. L. Nat. Prod. Lett. 1998, 11, 241-250.
16. Generic products will be reported elsewhere.
17. Compound 9 was observed when adding MeLi to 3, but 9 was not observed when adding MeMgBr to 3. The two pathways shown below may explain the formation of 9. One involves a 1,5-sigmatropic shift while the other one involves an intermolecular deprotonation of E, which could arise by a divergent collapse of intermediate B (Scheme 1). (Matrix Presented)