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Organic and Biomolecular Chemistry

Volumn 7, Issue 1, 2009, Pages 41-42

Thermal epimerization of diastereomeric Grignard reagents

(2) Beckmann, Jens a Schütrumpf, Alexandra a

a FREIE UNIVERSITÄT BERLIN (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOMERIC; EPIMERIZATION; GRIGNARD REAGENTS;

EID: 57549092077 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b819178f Document Type: Article

Times cited : (6)

References (9)

1
- 0003529785
- G. S. Silverman and P. E. Rakita, Marcel Dekker, New York
- Handbook of Grignard Reagents, ed., G. S. Silverman and, P. E. Rakita, Marcel Dekker, New York, 1996
- (1996) Handbook of Grignard Reagents, Ed.

2
- 1442360812
- and references cited therein
- R. W. Hoffmann Chem. Soc. Rev. 2003 32 225
- (2003) Chem. Soc. Rev. , vol.32 , pp. 225
- Hoffmann, R.W.¹

3
- 33749869312
- J. Beckmann D. Dakternieks M. Dräger A. Duthie Angew. Chem., Int. Ed. 2006 45 6509
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 6509
- Beckmann, J.¹ Dakternieks, D.² Dräger, M.³ Duthie, A.⁴

4
- 0009559358
- and references cited therein
- A. Hill J. Org. Chem 1966 31 20
- (1966) J. Org. Chem , vol.31 , pp. 20
- Hill, A.¹

5
- 57549112996
- Synthesis of the bornyl and fenchyl Grignard reagent. A solution of isobornyl chloride or β-fenchyl chloride (17.2 g, 100 mmol) in THF (180 mL) was slowly added to a suspension of activated Mg turnings (2.7 g, 110 mmol) in THF (20 mL). After the addition was completed, the mixture was heated under reflux for 12 h. Prior to use, the clear solution was separated from the excess of Mg via cannula. The yield determined by titration was about 80%. Synthesis of the epimerized bornyl and fenchyl Grignard reagent. A solution of the bornyl or fenchyl Grignard reagent was slowly distilled while toluene (220 mL) was constantly added to replace the original solvent THF. The temperature was slowly raised to 111 °C and kept there for 12 h. The yield determined by titration was between 65 and 75%
- Synthesis of the bornyl and fenchyl Grignard reagent. A solution of isobornyl chloride or β-fenchyl chloride (17.2 g, 100 mmol) in THF (180 mL) was slowly added to a suspension of activated Mg turnings (2.7 g, 110 mmol) in THF (20 mL). After the addition was completed, the mixture was heated under reflux for 12 h. Prior to use, the clear solution was separated from the excess of Mg via cannula. The yield determined by titration was about 80%. Synthesis of the epimerized bornyl and fenchyl Grignard reagent. A solution of the bornyl or fenchyl Grignard reagent was slowly distilled while toluene (220 mL) was constantly added to replace the original solvent THF. The temperature was slowly raised to 111 °C and kept there for 12 h. The yield determined by titration was between 65 and 75%

6
- 57549091903
- note
- 119Sn NMR spectrum revealed signals at δ-49.0 (integral 13%), -85.5 (integral 5%), -123.5 (integral 57.5%) and -126.4 (integral 14.5%), which were assigned to unreacted triphenyltin chloride, triphenyltin hydroxide, α-fenchyltriphenyltin (4a) and β-fenchyltriphenyltin (4b), respectively

7
- 33847804503
- D. Doddrell I. Burfitt W. Kitching M. Bullpitt C.-H. Lee R. J. Mynott J. L. Considine H. G. Kuivila R. H. Sarma J. Am. Chem. Soc. 1974 96 1640
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 1640
- Doddrell, D.¹ Burfitt, I.² Kitching, W.³ Bullpitt, M.⁴ Lee, C.-H.⁵ Mynott, R.J.⁶ Considine, J.L.⁷ Kuivila, H.G.⁸ Sarma, R.H.⁹

8
- 33644924126
- 3 (δ 117.1).
- A. Krasovskiy P. Knochel Synthesis 2006 890
- (2006) Synthesis , pp. 890
- Krasovskiy, A.¹ Knochel, P.²

9
- 5244357720
- D. Marton U. Russo D. Stivanello G. Tagliavini Organometallics 1996 15 1645
- (1996) Organometallics , vol.15 , pp. 1645
- Marton, D.¹ Russo, U.² Stivanello, D.³ Tagliavini, G.⁴

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