Hydrophobic effects in a simple Diels-Alder reaction in water

Tetrahedron Letters

Volumn 47, Issue 23, 2006, Pages 3957-3958

  Sarma, Diganta ^a   Pawar, Sanjay S ^a   Deshpande, Suvarna S ^a   Kumar, Anil ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

WATER;

ARTICLE; CHEMICAL REACTION; DIELS ALDER REACTION; GEOMETRY; HYDROPHOBICITY;

BETULACEAE;

EID: 33646135991     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.093     Document Type: Article

References (12)

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6. For example see:. Breslow R. Acc. Chem. Res. 24 (1991) 159-164
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9. 7 Deionized water was used for carrying out the reactions. The organic solvents (purity > 99+%, spectrophotometric grade) were used in the investigation. In a typical run, 0.6 mL (7.24 mmol) of freshly cracked 1 was transferred into 5 mL of solvent. Then 0.6 mL (6.44 mmol) of 2a was dissolved in 5 mL of the solvent. The solution containing 1 was added to the solution containing 2a. The reaction mixture was magnetically stirred at 27 °C for about 12 h. The stereochemical assignments were made by condensing crotonic acid with 1 and the resultant endo and exo bicylic acids separated by iodolactonization as described by. Evans D.A., Chapman K.T., and Bisaha J. J. Am. Chem. Soc. 110 (1988) 1238-1256
10. 1H NMR spectrum of the endo ester is also reported by. Ikota N. Chem. Pharm. Bull. 37 (1989) 2219-2221 The products were analyzed by gas chromatography using a CP SIL 5CB column. The retention times for the endo and exo products were 8.411 and 8.278 min, respectively. GC analyses of the individual isomers were found to be 8.633 min for the endo and 8.249 min for the exo ester. GC and NMR were also used to check the dimerization of 1, which was found to be negligible
11. Deshpande S.S., and Kumar A. Tetrahedron 58 (2002) 8759-8762
12. Pawar S.S., Phalgune U., and Kumar A. J. Org. Chem. 64 (1999) 7055-7060