SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 119, Issue 12, 1997, Pages 2832-2838

Stabilized and persistent allenylketenes

(4) Huang, Wenwei a Fang, Decai a,b Temple, Karen a Tidwell, Thomas T a

a UNIVERSITY OF TORONTO (Canada)

b BEIJING NORMAL UNIVERSITY (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; DRUG STABILITY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030972341 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja963496m Document Type: Article

Times cited : (34)

References (64)

1
- 33845470390
- (a) Kirmse, W.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7989-7991.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 7989-7991
- Kirmse, W.¹ Rondan, N.G.² Houk, K.N.³

2
- 0000203981
- (b) Niwayama, S.; Kallel, E. A.; Spellmeyer, D. C.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2813-2825.
- (1996) J. Org. Chem. , vol.61 , pp. 2813-2825
- Niwayama, S.¹ Kallel, E.A.² Spellmeyer, D.C.³ Sheu, C.⁴ Houk, K.N.⁵

3
- 33748222868
- (a) Murakami, M.; Amii, H.; Itami, K.; Ito, Y. Angew Chem., Int. Ed. Engl. 1995, 34, 1476-1477.
- (1995) Angew Chem., Int. Ed. Engl. , vol.34 , pp. 1476-1477
- Murakami, M.¹ Amii, H.² Itami, K.³ Ito, Y.⁴

4
- 0001693774
- (b) Pasto, D. J.; Kong, W. J. Org. Chem. 1989, 54, 4028-4033.
- (1989) J. Org. Chem. , vol.54 , pp. 4028-4033
- Pasto, D.J.¹ Kong, W.²

5
- 0029947240
- (c) Lopez, S.; Rodriquez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem. Soc. 1996, 118, 1881-1891.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 1881-1891
- Lopez, S.¹ Rodriquez, J.² Rey, J.G.³ De Lera, A.R.⁴

6
- 0027433936
- (d) Rey, J. G.; Rodriquez, J.; de Lera, A. R. Tetrahedron Lett. 1993, 34, 6293-6296.
- (1993) Tetrahedron Lett. , vol.34 , pp. 6293-6296
- Rey, J.G.¹ Rodriquez, J.² De Lera, A.R.³

7
- 0000679201
- (a) Pasto, D. J.; Yang, S.-H. J. Org. Chem. 1989, 54, 3544-3549.
- (1989) J. Org. Chem. , vol.54 , pp. 3544-3549
- Pasto, D.J.¹ Yang, S.-H.²

8
- 0004847062
- (b) Saalfrank, R. W.; Welch, A.; Haubner, M.; Bauer, U. Liebigs Ann. 1996, 171-181.
- (1996) Liebigs Ann. , pp. 171-181
- Saalfrank, R.W.¹ Welch, A.² Haubner, M.³ Bauer, U.⁴

9
- 1842358785
- (c) Hopf, H. Angew. Chem., Int. Ed. Engl. 1970, 9, 432.
- (1970) Angew. Chem., Int. Ed. Engl. , vol.9 , pp. 432
- Hopf, H.¹

10
- 33947335843
- (d) Huntsman, W. D.; Wristers, H. J. J. Am. Chem. Soc. 1967, 89, 342-347.
- (1967) J. Am. Chem. Soc. , vol.89 , pp. 342-347
- Huntsman, W.D.¹ Wristers, H.J.²

11
- 0000678751
- (a) Niwayama, S.; Kallel, E. A.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2517-2522.
- (1996) J. Org. Chem. , vol.61 , pp. 2517-2522
- Niwayama, S.¹ Kallel, E.A.² Sheu, C.³ Houk, K.N.⁴

12
- 0000847903
- (b) Bibas, H.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1995, 117, 9582-9583.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 9582-9583
- Bibas, H.¹ Wong, M.W.² Wentrup, C.³

13
- 0003659115
- (c) Smith, L. I.; Hoehn, H. H. J. Am. Chem. Soc. 1939, 61, 2619-2624.
- (1939) J. Am. Chem. Soc. , vol.61 , pp. 2619-2624
- Smith, L.I.¹ Hoehn, H.H.²

14
- 0002225356
- (d) Moore, H. W.; Yerxa, B. R. Adv. Strain Org. Chem. 1995, 4, 81-162.
- (1995) Adv. Strain Org. Chem. , vol.4 , pp. 81-162
- Moore, H.W.¹ Yerxa, B.R.²

15
- 0000564645
- (e) Koo, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389-3404.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 3389-3404
- Koo, S.¹ Liebeskind, L.S.²

16
- 0029552624
- (f) Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341-8350.
- (1995) J. Org. Chem. , vol.60 , pp. 8341-8350
- Danheiser, R.L.¹ Casebier, D.S.² Firooznia, F.³

17
- 0000750712
- (g) Taing, M.; Moore, H. W. J. Org. Chem. 1996, 61, 329-340.
- (1996) J. Org. Chem. , vol.61 , pp. 329-340
- Taing, M.¹ Moore, H.W.²

18
- 0011180687
- (h) Petasis, N. A.; Fu, D.-K. Synlett 1996, 155-156.
- (1996) Synlett , pp. 155-156
- Petasis, N.A.¹ Fu, D.-K.²

19
- 0345748582
- (a) Chapman, O. L. Pure Appl. Chem. 1979, 51, 331-339.
- (1979) Pure Appl. Chem. , vol.51 , pp. 331-339
- Chapman, O.L.¹

20
- 0000372101
- (b) Trahanovsky, W. S.; Park, M. J. Am. Chem. Soc. 1973, 95, 5412.
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 5412
- Trahanovsky, W.S.¹ Park, M.²

21
- 84985611668
- (c) Maier, G.; Lage, H. W.; Reisenauer, H. P. Angew. Chem., Int. Ed. Engl. 1981, 20, 976-977.
- (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 976-977
- Maier, G.¹ Lage, H.W.² Reisenauer, H.P.³

22
- 0028147397
- (d) Boch, R.; Bradley, J. C.; Durst, T.; Scaiano, J. C. Tetrahedron Lett. 1994, 35, 19-22.
- (1994) Tetrahedron Lett. , vol.35 , pp. 19-22
- Boch, R.¹ Bradley, J.C.² Durst, T.³ Scaiano, J.C.⁴

23
- 0002226604
- (e) Shimada, K.; Akimoto, S.; Takikawa, Y.; Kabuto, C. Chem. Lett. 1994, 2283-2286.
- (1994) Chem. Lett. , pp. 2283-2286
- Shimada, K.¹ Akimoto, S.² Takikawa, Y.³ Kabuto, C.⁴

24
- 1842266251
- (f) Toda, F.; Todo, E. Bull. Chem. Soc. Jpn. 1976, 49, 2645-2646.
- (1976) Bull. Chem. Soc. Jpn. , vol.49 , pp. 2645-2646
- Toda, F.¹ Todo, E.²

25
- 0004565018
- (g) Xu, S. L.; Moore, H. W. J. Org. Chem. 1992, 57, 326-338.
- (1992) J. Org. Chem. , vol.57 , pp. 326-338
- Xu, S.L.¹ Moore, H.W.²

26
- 0000418871
- (a) McAllister, M. A.; Tidwell, T. T. J. Org. Chem. 1994, 59, 4506-4515.
- (1994) J. Org. Chem. , vol.59 , pp. 4506-4515
- McAllister, M.A.¹ Tidwell, T.T.²

27
- 0001741998
- (b) Gong, L.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1991, 113, 6021-6028.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 6021-6028
- Gong, L.¹ McAllister, M.A.² Tidwell, T.T.³

28
- 0000065385
- (c) McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1994, 116, 7233-7238.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 7233-7238
- McAllister, M.A.¹ Tidwell, T.T.²

29
- 0003828015
- Wiley: New York, NY
- (a) Tidwell, T. T. Ketenes; Wiley: New York, NY, 1995.
- (1995) Ketenes
- Tidwell, T.T.¹

30
- 11944250881
- (b) Allen, A. D.; Ma, J.; McAllister, M. A.; Tidwell, T. T.; Zhao, D.-c. Acc. Chem. Res. 1995, 28, 265-271.
- (1995) Acc. Chem. Res. , vol.28 , pp. 265-271
- Allen, A.D.¹ Ma, J.² McAllister, M.A.³ Tidwell, T.T.⁴ Zhao, D.-C.⁵

31
- 0001768316
- (c) Zhao, D.-c.; Allen, A. D.; Tidwell, T. T. J. Am. Chem. Soc. 1993, 115, 10097-10103.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 10097-10103
- Zhao, D.-C.¹ Allen, A.D.² Tidwell, T.T.³

32
- 0343157513
- (d) Allen, A. D.; Lai, W.-Y.; Ma, J.; Tidwell, T. T. J. Am. Chem. Soc. 1994, 116, 2625-2626.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 2625-2626
- Allen, A.D.¹ Lai, W.-Y.² Ma, J.³ Tidwell, T.T.⁴

33
- 0344813483
- (e) Allen, A. D.; Lough, A. J.; Tidwell, T. T. J. Chem. Soc., Chem. Commun. 1996, 2171-2172.
- (1996) J. Chem. Soc., Chem. Commun. , pp. 2171-2172
- Allen, A.D.¹ Lough, A.J.² Tidwell, T.T.³

34
- 37049084202
- (f) Allen, A. D.; Ma, J.; McAllister, M. A.; Tidwell, T. T.; Zhao, D.-c. J. Chem. Soc., Perkin Trans. 2 1995, 847-851.
- (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 847-851
- Allen, A.D.¹ Ma, J.² McAllister, M.A.³ Tidwell, T.T.⁴ Zhao, D.-C.⁵

35
- 0000770422
- (a) Wang, K. K. Chem. Rev. 1996, 96, 207-222.
- (1996) Chem. Rev. , vol.96 , pp. 207-222
- Wang, K.K.¹

36
- 0026045597
- (b) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1415.
- (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1387-1415
- Nicolaou, K.C.¹ Dai, W.-M.²

37
- 0001380819
- (c) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057-8059.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8057-8059
- Myers, A.G.¹ Kuo, E.Y.² Finney, N.S.³

38
- 0027437682
- (d) Toshima, K.; Ohta, K.; Ohtsuka, A.; Matsumura, S.; Nakata, M. J. Chem. Soc., Chem. Commun. 1993, 1406-1407.
- (1993) J. Chem. Soc., Chem. Commun. , pp. 1406-1407
- Toshima, K.¹ Ohta, K.² Ohtsuka, A.³ Matsumura, S.⁴ Nakata, M.⁵

39
- 0000847502
- (e) Wang, K. K.; Wang, Z.; Sattsangi, P. D. J. Org. Chem. 1996, 61, 1516-1518.
- (1996) J. Org. Chem. , vol.61 , pp. 1516-1518
- Wang, K.K.¹ Wang, Z.² Sattsangi, P.D.³

40
- 0028293297
- (f) Nakatani, K.; Isoe, S.; Maekawa, S.; Saito, I. Tetrahedron Lett. 1994, 35, 605-608.
- (1994) Tetrahedron Lett. , vol.35 , pp. 605-608
- Nakatani, K.¹ Isoe, S.² Maekawa, S.³ Saito, I.⁴

41
- 0028972693
- (g) Nakatani, K.; Maekawa, S.; Tanabe, K.; Saito, I. J. Am. Chem. Soc. 1995, 117, 10635-10644.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 10635-10644
- Nakatani, K.¹ Maekawa, S.² Tanabe, K.³ Saito, I.⁴

42
- 0028275758
- (h) Sullivan, R W.; Coghlan, V. M.; Munk, S. A.; Reed, M. A.; Moore, H. W. J. Org. Chem. 1994, 59, 2276-2278.
- (1994) J. Org. Chem. , vol.59 , pp. 2276-2278
- Sullivan, R.W.¹ Coghlan, V.M.² Munk, S.A.³ Reed, M.A.⁴ Moore, H.W.⁵

43
- 0000480560
- (a) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927.
- (1980) J. Org. Chem. , vol.45 , pp. 3925-3927
- Danheiser, R.L.¹ Carini, D.J.²

44
- 33845185373
- (b) Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407-4413.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 4407-4413
- Danheiser, R.L.¹ Stoner, E.J.² Koyama, H.³ Yamashita, D.S.⁴ Klade, C.A.⁵

45
- 1842318250
- (c) Peterson, P. E.; Jensen, B. L. Tetrahedron Lett. 1984, 25, 5711-5714.
- (1984) Tetrahedron Lett. , vol.25 , pp. 5711-5714
- Peterson, P.E.¹ Jensen, B.L.²

46
- 0001453658
- (d) Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366-5367.
- (1995) J. Org. Chem. , vol.60 , pp. 5366-5367
- Jin, J.¹ Smith, D.T.² Weinreb, S.M.³

47
- 0001442002
- (e) Billups, W. E.; Haley, M. M. J. Am. Chem. Soc. 1991, 113, 5084-5085.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5084-5085
- Billups, W.E.¹ Haley, M.M.²

48
- 0004133516
- Gaussian, Inc.: Pittsburgh, PA
- Gaussian 92, Revision C. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Goperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1992.
- (1992) Gaussian 92, Revision C
- Frisch, M.J.¹ Trucks, G.W.² Head-Gordon, M.³ Gill, P.M.W.⁴ Wong, M.W.⁵ Foresman, J.B.⁶ Johnson, B.G.⁷ Schlegel, H.B.⁸ Robb, M.A.⁹ Replogle, E.S.¹⁰ Goperts, R.¹¹ Andres, J.L.¹² Raghavachari, K.¹³ Binkley, J.S.¹⁴ Gonzalez, C.¹⁵ Martin, R.L.¹⁶ Fox, D.J.¹⁷ Defrees, D.J.¹⁸ Baker, J.¹⁹ Stewart, J.J.P.²⁰ Pople, J.A.²¹ more..

49
- 0000164127
- (a) Brown, R. D.; Godfrey, P. D.; Woodruff, M. Aust. J. Chem. 1979, 32, 2103-2109.
- (1979) Aust. J. Chem. , vol.32 , pp. 2103-2109
- Brown, R.D.¹ Godfrey, P.D.² Woodruff, M.³

50
- 0001490724
- (b) Trahanovsky, W. S.; Surber, B. W.; Wilkes, M. C.; Preckel, M. M. J. Am. Chem. Soc. 1982, 104, 6779-6781.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 6779-6781
- Trahanovsky, W.S.¹ Surber, B.W.² Wilkes, M.C.³ Preckel, M.M.⁴

51
- 0027454390
- (a) Ezcurra, J. E.; Moore, H. W. Tetrahedron Lett. 1993, 34, 6177-6180.
- (1993) Tetrahedron Lett. , vol.34 , pp. 6177-6180
- Ezcurra, J.E.¹ Moore, H.W.²

52
- 0038219712
- (b) Ezcurra, J. E.; Pham, C.; Moore, H. W. J. Org. Chem. 1992, 57, 4787-4789.
- (1992) J. Org. Chem. , vol.57 , pp. 4787-4789
- Ezcurra, J.E.¹ Pham, C.² Moore, H.W.³

53
- 84982072876
- (c) Ried, W.; Knorr, H.; Knorr, U. Chem. Ber. 1976, 109, 1506-1515.
- (1976) Chem. Ber. , vol.109 , pp. 1506-1515
- Ried, W.¹ Knorr, H.² Knorr, U.³

54
- 33947093052
- (d) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611-3613.
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 3611-3613
- Tebbe, F.N.¹ Parshall, G.W.² Reddy, G.S.³

55
- 0029114745
- (e) Petasis, N. A.; Hu, Y.-H.; Fu, D.-K. Tetrahedron Lett. 1995, 36, 6001-6004.
- (1995) Tetrahedron Lett. , vol.36 , pp. 6001-6004
- Petasis, N.A.¹ Hu, Y.-H.² Fu, D.-K.³

56
- 1842396499
- Allen, A. D.; Colomvakos, J. D.; Egle, I.; Ma, J.; Marra, R.; Tidwell, T. T. Chem. Lett. 1996, 45-46.
- (1996) Chem. Lett. , pp. 45-46
- Allen, A.D.¹ Colomvakos, J.D.² Egle, I.³ Ma, J.⁴ Marra, R.⁵ Tidwell, T.T.⁶

57
- 1842342220
- 3 and H of 10.9 and 3.3 kcal/mol, respectively (ref. 6b)
- 3 and H of 10.9 and 3.3 kcal/mol, respectively (ref. 6b).

58
- 0003887404
- Harper and Row: New York, NY
- (b) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper and Row: New York, NY, 1987; pp 194-195.
- (1987) Mechanism and Theory in Organic Chemistry , pp. 194-195
- Lowry, T.H.¹ Richardson, K.S.²

59
- 1842303950
- note
- 3, 8; R = 0.0370, GOF = 0.925. Full crystallographic data are given in the Supporting Information.

60
- 0003942864
- Wiley: New York, NY, Chapter 14
- (a) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, NY, 1994; Chapter 14.
- (1994) Stereochemistry of Organic Compounds
- Eliel, E.L.¹ Wilen, S.H.²

61
- 33947085764
- (b) Garratt, P. J.; Nicolaou, K. C.; Sondheimer, F. J. Am. Chem. Soc. 1973, 95, 4582-4592.
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 4582-4592
- Garratt, P.J.¹ Nicolaou, K.C.² Sondheimer, F.³

62
- 37049130415
- (c) Kleveland, K.; Skattebøl, L. J. Chem. Soc., Chem. Commun. 1973, 432-433.
- (1973) J. Chem. Soc., Chem. Commun. , pp. 432-433
- Kleveland, K.¹ Skattebøl, L.²

63
- 0037791240
- (d) Lin, J.; Pang, Y.; Young, V. G., Jr.; Barton, T. J. J. Am. Chem. Soc. 1993, 115, 3794-3795.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 3794-3795
- Lin, J.¹ Pang, Y.² Young Jr., V.G.³ Barton, T.J.⁴

64
- 33845183891
- (e) Johnson, R. P. Chem. Rev. 1989, 89, 1111-1124.
- (1989) Chem. Rev. , vol.89 , pp. 1111-1124
- Johnson, R.P.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.