Synthesis and reaction of 1,2-allenyl ketones

Chinese Journal of Organic Chemistry

Volumn 20, Issue 6, 2000, Pages 850-860

  Li, Lin Tao ^a   Ma, Sheng Ming ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allenyl ketone; Reaction; Synthesis

Indexed keywords

EID: 0034355185     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (110)

1. H F Schuster, G M Coppda. "Allenes in Organic Synthesis", John Wiley&Sons: New York, 1988
2. F Y Perveer. Gen. Chem. USSR, 1948, 18, 686
3. A S K Hashmi, T L Ruppert, T Knöfel, J W Bats. J. Org. Chem. , 1997, 62, 7295
4. A S K Hashmi, L Schwarz. Chem. Ber. , 1997, 130, 1449
5. J A Marshall, X J Wang. J. Org. Chem. , 1992, 57, 3387
6. J A Marshall, G S Bartley. J. Org. Chem. , 1994, 59, 7169
7. J A Marshall, C A Sehon. J. Org. Chem. , 1997, 62, 4313
8. J A Marshall, E D Robinson. J. Org. Chem. , 1990, 55, 3450
9. Y Fukuda, H Shiragami, K Utimoto, H Nozaki. J. Org. Chem. , 1991, 56, 5816
10. H B Henbest. J. Chem. Soc. , 1952, 4536
11. M Bertrand, J L Gras, M Delépine. Compt. Rend. , 1962, 252, 1305
12. M Bertrand, M Delépine. Compt. Rend. , 1957, 244, 1790
13. M Bertrand, J L Gras. Bull. Soc. Chim. Fr. , 1962, 2136
14. D D Halton, G A Morrison. J. Chem. Research (s), 1979, 4
15. L Brandsma, H D Verkruijsse. "Synthesis of Acetylenes, Allenes and Cumulenes" Elsevier: Amsterdan, 1981, P.101 and P.236
16. W D Huntsman, T K Yin. J. Org. Chem. , 1983, 48, 3813
17. C Bruneau, P H Dixneuf. in "Comprehensive Organic Functional Group Transformations", A R Katritzky, O Meth-Coln, C W Rees. eds, Elsevier: Oxford, 1995, vol. 1, P.953
18. T Nagasawa, K Taya, M Kitamura, K Suzuki. J. Am. Chem. Soc. , 1996, 118, 8949
19. R C Larock, M S Chow, S J Smith. J. Org. Chem. , 1986, 51, 2623
20. A S K Hashmi, J W Bats, J H Choi, L Schwarz. Tetrahedron Lett. , 1998, 39, 7491
21. (a) R Couffignal, M Gaudemar. Bull. Soc. Chim. Fr. , 1970, 3157
22. (b) R Couffignal, M Gaudemar. Bull. Soc. Chim. Fr. , 1969, 898
23. R Couffignal, M Gaudemar. Bull. Soc. Chim. Fr. , 1969, 3218
24. R Couffignal, M Gaudemar. , M G Champetier. C. R. Acat. Sc. Paris, t. , 1968, 266, 224
25. F Gaudemar-Bardone, C Dufraisse. Compt. Rend. , 1956, 243, 1895
26. F Gaudemar-Bardone. Ann. Chim. (Paris), 1958, 3, 52
27. (a) J C Clinet, G Linstrumelle. Chem. Lett. , 1994, 389
28. (b) J C Clinet, G Linstrumelle. Chem. Lett. , 1994, 597
29. J C Clinet, G Linstrumelle. Nouv. J. Chem. , 1977, 1, 373
30. J M Dollat, J L Luche, P Crabbé. J. Chem. Soc. Chem. Commum. , 1977, 761
31. M Franck-Neumann, F Brion. Angew. Chem. , 1979, 91, 736
32. S W Russell, B C L Weedon. Chem. Commum. , 1969, 85
33. (a) P D Landor, S R Landor, S Mukasa. Chem. Commum. , 1971, 1638
34. (b) P D Landor, S R Landor, O Odyek. J. Chem. Soc. Perkin I, 1977, 93
35. J H Osaka. Pharm. Bull. (Japan), 1956, 4, 89
36. J A Mashall, X J Wang. J. Org. Chem. , 1991, 56, 960
37. K M Wu, M M Midland, W H Okamura. J. Org. Chem. , 1990, 55, 4381
38. M Bertrand, G Gll, J Viala. Tetrahedron Lett. , 1979, 18, 1595
39. B Cazes, Sy Julia. Synth. Commum. , 1977, 273
40. P Cresson, M H Normant. C. R. Acad. Sc. Paris, 1977, 284, 247
41. J A Reuter, R G Salomon. Tetrahedron Lett. , 1978, 35, 3199
42. G Saucy, R Marbet. Helv. Chim. Acta, 1967, 50, 1159
43. Z Hamlet, W D Barker. Synthesis, 1970, 543
44. G Aksnes, P Fryen. Acta. Chem. Scand. , 1968, 22, 2343
45. M Dupré, H Strzelecka. C. R. Acad. Sc. Paris, 1972, 274, 1091
46. N A Petasis, K A Teets. J. Am. Chem. Soc. , 1992, 114, 10328
47. G Buono. Tetrahedron Lett. , 1972, 32, 3257
48. G Buono. Synthesis, 1981, 872
49. N R Rosenquist, O L Chapman. J. Org Chem. , 1976, 41, 3326
50. C Rouvier, M Bertrand, M Delépine. C. R. Acad. Sc. Paris, 1964, 259, 1530
51. (a) M Bertrand, C Rouvier. Bull. Soc. Chim. Fr. , 1968, 2533
52. (b) M Bertrand, C Rouvier. Bull. Soc. Chim. Fr. , 1968, 2537
53. W Ried, R Neidhardt. Chem. Ber. , 1970, 103, 2208
54. F Toda, M Yamamoto, K Tanaffa. Tetrahedron Lett. , 1985, 26, 631
55. R F Cunico. Tetrahedron Lett. , 1994, 35, 2291
56. R F Cunico, K Nair. Synth. Commun. , 1996, 26, 803
57. J P Pillot, B Bennetau, J Dunogues, R Calas. Tetrahedron Lett. , 1981, 22, 3401
58. T J Barton, J G P Hussmann. J. Am. Chem. Soc. , 1983, 105, 6316
59. T L Gilchrist, D P Pearson. J. Chem. Soc. Perkin I, 1976, 989
60. H M Berstermann, R Harder, H Winter, C Wentrup. Angew. Chem. , 1979, 92, 555
61. T Mandai, H Kunitomi, K Higashi, M Kawada, J Tsuji. Synlett. , 1991, 697
62. M Bertrand, J L Gras. C. R. Acad. Sc. Paris, 1965, 260, 6926
63. H J Cristau, J Viala, H Christol. Tetrahedron Lett. , 1982, 23, 1569
64. H J Cristau, J Viala, H Christol. Bull. Soc. Chim. Fr. , 1985, 980
65. J L Gras, B S Gallédou. Bull. Soc. Chim. Fr. , 1983, II-89
66. (a) S Ma, Z Shi, L Li. J. Org. Chem. , 1998, 63, 4522
67. (b) S Ma, L Li, H Xie. J. Org. Chem. , 1999, 64, 5325
68. R L Bol'shedvorskaya, G A Pavlova, L D Garrilov, N V Alekseeva, L I Vereshchagin. J. Org. Chem. USS, 1972, 8, 1927
69. I Tämnefors, A Clasesson, M Karlsson. Acta. Pharm. Suec. , 1975, 12, 435
70. T Sugita, M Eida, H Ito, N Komatsu, K Abe, M Suama. J. Org. Chem. , 1987, 52, 3789
71. M Bertrand, M Deline. C. R. Acad. Sc. Ser. C. , 1957, 245, 2306
72. C Santelli. Tetrahedron Lett. , 1980, 21, 2893
73. G Buono, G Peiffer. Tetrahedron Lett. , 1972, 149
74. G Buono, J R Llinas. J. Am. Chem. Soc. , 1981, 103, 4532
75. A Peiffer, A Guillemonat, G Buono. Bull. Soc. Chim. Fr. , 1969, 946
76. G Buono, G Peiffer, A Guillemonat. C. R. Acad. Sc. Paris, t. , 1970, 271c, 937
77. J Berlan, J P Battioni, K Koosha. Tetrahedron Lett. , 1976, 3355
78. M Bertrand, J G Gll, Viala. Tetrahedron Lett. , 1977, 1785
79. J Berlan, K Koosha. J. Organometallic Chem. , 1978, 153, 99
80. J Berlan, K Koosha. J. Organometallic Chem. , 1978, 153, 359
81. J Berlan, J P Battioni, K Koosha. Bull. Soc. Chem. Fr. , 1979, II-183
82. M Bertrand, J L Gras. Bull. Soc. Chem. Fr. , 1962, 2136
83. M Bertrand, J L Gras. Bull. Soc. Chem. Fr. , 1968, 1534
84. J A Marshall, Y Tang. J Org. Chem. , 1993, 58, 3233
85. S Ma, S Zhao. J. Am. Soc. Chem. 1999, 121, 2136
86. M Bertrand, J L Gras. Compt. Rend. , 1962, 255, 1305
87. M Bertrand, M Santelli, M Mousseron. Compt. Rend. , 1966, 262, 1601
88. J L Gras. J. Chem. Research(s), 1982, 300
89. R Gleiter, T Herb, O Borzyk, I Hyla-Kryspin. Liebigs Ann. , 1995, 357
90. J L Gras, B S Galledou, M Bertrand. Bull. Soc. Chim. Fr. , 1988, 757
91. M Bertrand, J L Gras, B S Galledou. Tetrahedron Lett. , 1978, 32, 2873
92. M Bertrand, J L Gras. Bull. Soc. Chim. Fr. , 1967, 4336
93. M Bertrand, J L Gras. C. R. Acad. Sc. Paris, t. , 1964, 259, 404
94. (a) V R Gleiter, C Sigwart. J. Org. Chem. , 1994, 59, 1027
95. (b) V R Gleiter, C Sigwart, B Kissler. Angew. Chem. , 1989, 101, 1561
96. R Sánchez-Obregón, H Barrios, B Ortfz, F Yuste. Rev. Roum. Chim. , 1986, 31, 709
97. (a) P Barrioni, A Aspect, L VoQung, Y VoQung. C. R. Acad. Sci. , Ser. C, 1969, 268, 1233
98. (b) P Battioni, A Aspect, L VoQung, Y VoQung. Bull. Soc. Chim. Fr. , 1978, II-401
99. P Barrioni, A Aspect, L VoQung, Y VoQung. Bull. Soc. Chim. Fr. , 1978, II-415
100. J Jullien, J M Pechine, F Perez, J J Piade. Tetrahedron, 1982, 38, 1413
101. W D Huntsman, T K Yin. J. Org. Chem. , 1983, 48, 3813
102. J A Mashall, X J Wang. J. Org. Chem. , 1991, 56, 960
103. J A Mashall, C A Sehon. J. Org. Chem. , 1995, 60, 5966
104. J A Mashall, E M Wallace. J. Org. Chem. , 1995, 60, 796
105. J A Mashall, J Liao. J. Org. Chem. , 1998, 63, 5962
106. A S K Hashmi. Angew. Chem. Int. Ed. Engl. , 1995, 34, 1581
107. (a) Y Nagao, W S Lee, Y Komaki, S Sano, M Shiro. Chem. lett. , 1994, 597
108. (b) Y Nagao, W S Lee, K Kim. Chem. Lett. , 1994, 389
109. Y Nagao, W S Lee, I Y Jeong, M Shiro. Tetrahedron Lett. , 1995, 36, 2799
110. A S K Hashmi, L Schwarz . M Bohe. Tetrahedron Lett. , 1998, 39, 8969