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Advanced Synthesis and Catalysis

Volumn 338, Issue 7, 1996, Pages 647-653

Reaction of 5a-bromo-α-tocopherol with nucleophiles

(2) Rosenau, T a Habicher, W D a

a DRESDEN UNIVERSITY OF TECHNOLOGY (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3042879227 PISSN: 16154150 EISSN: None Source Type: Journal
DOI: None Document Type: Article

Times cited : (4)

References (14)

1
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- For the preceding paper see: T. Rosenau, W. D. Habicher, J. Org. Chem. 60 (1995) 8121
- (1995) J. Org. Chem. , vol.60 , pp. 8121
- Rosenau, T.¹ Habicher, W.D.²

2
- 0029022577
- T. Rosenau, W. D. Habicher, Tetrahedron 51 (1995) 7919
- (1995) Tetrahedron , vol.51 , pp. 7919
- Rosenau, T.¹ Habicher, W.D.²

3
- 0001208059
- For preparation see: D. R. Nelan, C. D. Robeson, J. Am. Chem. Soc. 84 (1962) 2963; P. Schudel, H. Mayer, J. Metzger, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 636. For NMR data see: H. M. Fales, J. Chem. Soc., Perkin Trans. II 1990 1005
- (1962) J. Am. Chem. Soc. , vol.84 , pp. 2963
- Nelan, D.R.¹ Robeson, C.D.²

4
- 84981840357
- For preparation see: D. R. Nelan, C. D. Robeson, J. Am. Chem. Soc. 84 (1962) 2963; P. Schudel, H. Mayer, J. Metzger, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 636. For NMR data see: H. M. Fales, J. Chem. Soc., Perkin Trans. II 1990 1005
- (1963) Helv. Chim. Acta , vol.46 , pp. 636
- Schudel, P.¹ Mayer, H.² Metzger, J.³ Rüegg, R.⁴ Isler, O.⁵

5
- 0001208059
- For preparation see: D. R. Nelan, C. D. Robeson, J. Am. Chem. Soc. 84 (1962) 2963; P. Schudel, H. Mayer, J. Metzger, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 636. For NMR data see: H. M. Fales, J. Chem. Soc., Perkin Trans. II 1990 1005
- J. Chem. Soc., Perkin Trans. II , vol.1990 , pp. 1005
- Fales, H.M.¹

6
- 0005231531
- For an illustrative example see: C. F. H. Allen, J. W. Gates jr., Org. Synth., Coll. Vol.III (1955) 140
- (1955) Org. Synth., Coll. , vol.3 , pp. 140
- Allen, C.F.H.¹ Gates Jr., J.W.²

7
- 3042864220
- note
- The silver salts have to be carefully liberated from water. In addition, satisfactory results were obtained only with finely powdered material.

8
- 84981835777
- P. Schudel, H. Mayer, J. Metzger, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 333; W. John, Z. Physiol. Chem. 252 (1938) 222
- (1963) Helv. Chim. Acta , vol.46 , pp. 333
- Schudel, P.¹ Mayer, H.² Metzger, J.³ Rüegg, R.⁴ Isler, O.⁵

9
- 84941483084
- P. Schudel, H. Mayer, J. Metzger, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 333; W. John, Z. Physiol. Chem. 252 (1938) 222
- (1938) Z. Physiol. Chem. , vol.252 , pp. 222
- John, W.¹

10
- 3042975598
- note
- +, are readily eliminated, analogous to the elimination of HBr from 5a-bromo-α-tocopherol (1). However, 5a-alkoxy-α-tocopherols or 5a-aryloxy-α-tocopherols and, especially, 5a-α-tocopheryl esters are not as thermolabile as 5a-bromo-α-tocopherol. Elimination of the substituents does not occur below 80°C.

11
- 2742578400
- IUPAC-IUB Commission on Biochemical Nomenclature (CBN), Arch. Biochim. Biophys. 165 (1974) 1; IUPAC-IUB Nomenclature of Tocopherols and Related Compounds, Eur. J. Biochem. 123 (1982) 473
- (1974) Arch. Biochim. Biophys. , vol.165 , pp. 1

12
- 0020122108
- IUPAC-IUB Commission on Biochemical Nomenclature (CBN), Arch. Biochim. Biophys. 165 (1974) 1; IUPAC-IUB Nomenclature of Tocopherols and Related Compounds, Eur. J. Biochem. 123 (1982) 473
- (1982) Eur. J. Biochem. , vol.123 , pp. 473

13
- 0019180922
- S. Urano, M. Matsuo, Chem. Pharm. Bull. 28 (1980) 1992, and S. Brownstein, K. U. Ingold, J. Org. Chem. 54 (1989) 561
- (1980) Chem. Pharm. Bull. , vol.28 , pp. 1992
- Urano, S.¹ Matsuo, M.²

14
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- S. Urano, M. Matsuo, Chem. Pharm. Bull. 28 (1980) 1992, and S. Brownstein, K. U. Ingold, J. Org. Chem. 54 (1989) 561
- (1989) J. Org. Chem. , vol.54 , pp. 561
- Brownstein, S.¹ Ingold, K.U.²

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