NBS-Promoted reactions of symmetrically hindered methylphenols via p- benzoquinone methide

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 108-115

  Baik, Woonphil ^a   Lee, Hyun Joo ^a   Jang, Jung Min ^a   Koo, Sangho ^a   Kim, Byeong Hyo ^b  

^a Myong Ji University   (South Korea)

^b Kwangwoon University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; CRESOL;

ARTICLE; CHEMICAL REACTION; MOLECULAR STABILITY; OXIDATION; STOICHIOMETRY;

EID: 0342615046     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9911185     Document Type: Article

References (76)

1. (a) Harkin, J. M.; Taylor, W. I.; Battersby, A. R. Oxidative Coupling of Phenols; Marcel Dekker Inc.: New York, 1967; pp 263-300.
2. (b) Omura, K. J. Org. Chem. 1992, 57, 306.
3. (c) Diao, L.; Yang, C.; Wan, P. J. Am. Chem. Soc. 1995, 117, 5369.
4. (d) Omura, K. J. Org. Chem. 1997, 62, 8790.
5. (e) Omura, K. J. Org. Chem. 1984, 49, 3046.
6. (f) Sheppard, W. A. J. Org. Chem. 1992, 57, 6883.
7. (g) For a review on quinone methides, see: Wagner, H. U.; Gompper, R. The Chemistry of Quinonoid Compounds; Patai, S., Ed.; John Wiley and Sons: New York, 1974; part 2, pp 1145-1178.
8. (a) Omura, S.; Tanaka, H.; Okada, Y.; Marumo, H. J. Chem. Soc., Chem. Commun. 1976, 320.
9. (b) St. Pyrek, J.; Achmatowicz, O.; Zamojski, A. Tetrahedron. 1977, 33, 673.
10. (c) Scott, A. I. Quarterly Rev. 1965, 1.
11. (d) Angle, S. R.; Turnbell, K. D. J. Am. Chem. Soc. 1990, 112, 3698.
12. (a) Roper, J. M.; Everly, C. R. J. Org. Chem. 1988, 53, 2639.
13. (b) McClure, J. D. J. Org. Chem. 1962, 27, 2365.
14. (c) Roper, J. M., U.S. Patent 4,480,133, 1984.
15. (d) Hatchard, W. R. J. Am. Chem. Soc. 1958, 80, 3640.
16. (a) Starnes, W. H.; Myers, J. A.; Lauff, J. J. J. Org. Chem. 1969, 34, 3404.
17. (b) Starnes, W. H.; Lauff, J. J. J. Org. Chem. 1970, 35, 1978.
18. (c) Becker, H.; Gustafsson, K. J. Org. Chem. 1976, 41, 214.
19. (d) Katritzky, A. R.; Zhang, Z.; Lang, H.; Lan, X. J. Org. Chem. 1994, 59, 7209.
20. For examples of calixarene p-quinone methide, see: (e) Gutsche, C. D.; Nam, K. C. J. Am. Chem. Soc. 1988, 110, 6153.
21. (f) Alan, I.; Sharma, S. K.; Gutsche, C. D. J. Org. Chem. 1994, 59, 3716.
22. 1H NMR spectroscopy in a dilute solution by Winstein. (a) Dyall, L. K.; Winstein, S. J. Am. Chem. Soc. 1972, 94, 2196. (b) Winstein, S.; Filar, L. J. Tetrahedron Lett. 1960, 25, 9.
23. 1H NMR spectroscopy in a dilute solution by Winstein. (a) Dyall, L. K.; Winstein, S. J. Am. Chem. Soc. 1972, 94, 2196. (b) Winstein, S.; Filar, L. J. Tetrahedron Lett. 1960, 25, 9.
24. 4f
25. 4f
26. 4f
27. 4f
28. 4f
29. 4f
30. 4f
31. 3I, reacts with triethyl phosphite to give phosphonate in 95% yield. See ref 4a and Dubs, P.; Stegmann, W.; Luisoli, R.; Martin, R. EP 434606 A1 910626; Chem. Abstr. 115, 136390.
32. (a) Angle, S. R.; Arnaiz, D. O.; Boyce, J. P.; Frutos, R. P.; Louie, M. S.; Mattson-Arnais, H. L.; Raineer, J. D.; Turnbull K. D.; Yang, W. J. Org. Chem. 1994, 59, 6322.
33. (b) Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1989, 111, 1136.
34. (c) Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Tetrahedron Lett. 1989, 30, 1193.
35. (d) Angle, S. R.; Rainier, J. D. J. Org. Chem. 1992, 57, 6883.
36. 22O.
37. Dalton, R. D.; Dutta, V. P.; Jones, D. C. J. Am. Chem. Soc. 1968, 90, 5498.
38. Wolfe, S.; Pilgrim, W. R.; Garrard, T. F.; Chamberlain, P. Can. J. Chem. 1971, 49, 1099.
39. (a) Kornblum, N.; Jones, W. J.; Anderson, G. J. J. Am. Chem. Soc. 1959, 81, 4113.
40. (b) Nace, H. R.; Monagle, J. J. J. Org. Chem. 1959, 24, 1792
41. (a) Pfitzer, K. E.; Moffatt, J. G. J. Am. Chem. Soc. 1965, 87, 5661.
42. (b) Smith, W. E. J. Org. Chem. 1972, 37, 3972.
43. (c) Nishinaga, A.; Shimizu, T.; Matsuura, T. Tetrahedron Lett. 1981, 22, 5293.
44. (d) Torssell, K. Tetrahedron Lett., 1966, 7, 4445.
45. The suggestion that the hydrogen-abstracting species by a succinimidyl radical might be involved in NBS allylic bromination has been presented. Skell, P. S.; Lindstrom, M. J.; Day, J. C. J. Am. Chem. Soc. 1974, 96, 5616.
46. (a) Omura, K. J. Org. Chem. 1991, 56, 921.
47. (b) Neureiter, N. P. J. Org. Chem. 1963, 28, 3486.
48. 4 is referred to as the reagent of choice. However, yields are poor to fair, and low regioselectivities have been observed. For example, the Duff reaction of 2,6-dimethoxyphenol gives 2b in 31% yield. For a representative example, see: Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X. J. Org. Chem. 1994, 59, 1939.
49. 2- enzyme lactase method, phenolic and benzylic hydroxyl groups require protection before oxidation of aromatic methyl groups. See: Potthast, A.; Rosenau, T.; Chen, C.-L.; Gratzl, J. S. J. Org. Chem. 1995, 60, 4320. For reviews on the oxidation of methylarenes to their aldehydes, see: (a) Wilberg, K. B. Oxidation in Organic Chemistry; Wilberg, K. B., Ed.; Academic: New York, 1965; pp 101-105. (b) Larock, R. C. Comprehensive Organic Transformation; VCH: New York; 1989; pp 591-592.
50. 2-enzyme lactase method, phenolic and benzylic hydroxyl groups require protection before oxidation of aromatic methyl groups. See: Potthast, A.; Rosenau, T.; Chen, C.-L.; Gratzl, J. S. J. Org. Chem. 1995, 60, 4320. For reviews on the oxidation of methylarenes to their aldehydes, see: (a) Wilberg, K. B. Oxidation in Organic Chemistry; Wilberg, K. B., Ed.; Academic: New York, 1965; pp 101-105. (b) Larock, R. C. Comprehensive Organic Transformation; VCH: New York; 1989; pp 591-592.
51. 2- enzyme lactase method, phenolic and benzylic hydroxyl groups require protection before oxidation of aromatic methyl groups. See: Potthast, A.; Rosenau, T.; Chen, C.-L.; Gratzl, J. S. J. Org. Chem. 1995, 60, 4320. For reviews on the oxidation of methylarenes to their aldehydes, see: (a) Wilberg, K. B. Oxidation in Organic Chemistry; Wilberg, K. B., Ed.; Academic: New York, 1965; pp 101-105. (b) Larock, R. C. Comprehensive Organic Transformation; VCH: New York; 1989; pp 591-592.
52. 2- enzyme lactase method, phenolic and benzylic hydroxyl groups require protection before oxidation of aromatic methyl groups. See: Potthast, A.; Rosenau, T.; Chen, C.-L.; Gratzl, J. S. J. Org. Chem. 1995, 60, 4320. For reviews on the oxidation of methylarenes to their aldehydes, see: (a) Wilberg, K. B. Oxidation in Organic Chemistry; Wilberg, K. B., Ed.; Academic: New York, 1965; pp 101-105. (b) Larock, R. C. Comprehensive Organic Transformation; VCH: New York; 1989; pp 591-592.
53. Markovac, A.; Stevens, C. L.; Ash, A. B.; Hackley, B. E. J. Org. Chem. 1970, 35, 841.
54. Majetich, G.; Hicks, R.; Reister, S. J. Org. Chem. 1997, 62, 4321. The mechanism accounts for the formation of bromomethylsulfonium bromide 8 from DMSO and HBr, see: Mislow, K.; S. Mmons, T.; Melillo, J.; Ternay, A. J. Am. Chem. Soc. 1964, 86, 1452.
55. Majetich, G.; Hicks, R.; Reister, S. J. Org. Chem. 1997, 62, 4321. The mechanism accounts for the formation of bromomethylsulfonium bromide 8 from DMSO and HBr, see: Mislow, K.; S. Mmons, T.; Melillo, J.; Ternay, A. J. Am. Chem. Soc. 1964, 86, 1452.
56. 4 is also well documented, see: (f) Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473. (g) Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
57. 4 is also well documented, see: (f) Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473. (g) Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
58. 4 is also well documented, see: (f) Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473. (g) Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
59. 4 is also well documented, see: (f) Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473. (g) Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
60. 4 is also well documented, see: (f) Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473. (g) Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
61. 4 is also well documented, see: (f) Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473. (g) Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
62. 4 is also well documented, see: (f) Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473. (g) Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
63. The site-selective bromination of arenes with aqueous HBr in DMSO has recently been reported. However, this report lacks of the varsity of arenes, and no example with NBS is appeared. See: Srivastava, S. K.; Chauhan, P. M. S.; Bhaduri, A. P. J. Chem. Soc., Chem. Commun. 1996, 2679.
64. The density functional theory calculations employed Becke's three parameter hybrid method (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) and the correlation functional of Lee (Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 785-789) within the Gaussian 94 program: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, w.; Wong, M. W.; Andres, J. L.; Repiogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Revision B.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
65. The density functional theory calculations employed Becke's three parameter hybrid method (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) and the correlation functional of Lee (Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 785-789) within the Gaussian 94 program: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, w.; Wong, M. W.; Andres, J. L.; Repiogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Revision B.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
66. The density functional theory calculations employed Becke's three parameter hybrid method (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) and the correlation functional of Lee (Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 785-789) within the Gaussian 94 program: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, w.; Wong, M. W.; Andres, J. L.; Repiogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Revision B.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
67. (a) Freeman, P. K. J. Am. Chem. Soc. 1998, 120, 1619.
68. (b) Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1987, 62, 4398.
69. (c) Ammann, J. R.; Subramanian, R.; Sheridan, R. S. J. Am. Chem. Soc. 1992, 114, 7592.
70. (d) Liu, J.; Niwayama, S.; You, Y.; Houk, K. N. J. Org. Chem. 1998, 63, 1064.
71. (e) Halton, B.; Cooney, M. J.; Boese, R.; Maulitz, A. H. J. Org. Chem. 1998, 63, 1583.
72. (a) Cohen, L. J. Org. Chem. 1957, 22, 1333.
73. (b) Allen, C. F. H.; Leubner, G. W. Org. Syntheses Coll. Vol. 4, 866.
74. (c). Unangst, P. C.; Conner, D. T.; Centenco, W. A.; Sorenson, R. J.; Kostlan, C. R.; Sircar, J. C.; Wright, C. D.; Schrier. D. J.; Dyer, R. D. J. Med. Chem. 1994, 37, 322.
75. (d) Matsuura, T.; Nagamachi, T.; Matsuo, K.; Nishinaga, A. J. Med. Chem. 1968, 11, 322.
76. (e) Smith, W. E. J. Org. Chem. 1972, 37, 3972.