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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 11
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Original Articles

A Convenient and Simplified Preparation of Both Enantiomers of α-Terpinyl Chloride

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Pages 1975-1983 | Received 19 Aug 1999, Published online: 04 Dec 2007

REFERENCES AND NOTES

  • Riban , J. 1874 . C. R. Hebd. Seances Acad. Sci. , 79 : 223
  • Ravindranath , B. and Srinivas , P. 1984 . Tetrahedron , 40 : 1623
  • Gurudutt , K. N. , Ravindranath , B. and Srinivas , P. 1982 . Tetrahedron , 38 : 1843
  • Gurudutt , K. N. , Rao , S. and Srinivas , P. 1991 . Indian J. Chem. , 30B : 343
  • Ravindranath , B. and Srinivas , P. 1985 . Indian J. Chem. , 24B : 1178
  • Wallach , O. and Kremers , E. 1888 . Liebigs Ann. Chem. , 245 : 241
  • Muraleedharan , N. V. and Verghese , J. 1971 . Curr. Sci. , 40 : 152
  • Wallach , O. 1888 . Liebigs Ann. Chem. , 245 : 241
  • Kropp , P. J. , Daus , K. A. , Crawford , S. D. , Tubergen , M. W. , Kepler , K. D. , Craig , S. L. and Wilson , V. P. 1990 . J. Am. Chem. Soc. , 112 : 7433
  • Kropp , P. J. and Crawford , S. D. 1994 . J. Org. Chem. , 59 : 3102
  • Boudjouk , P. , Kim , B.-K. and Han , B.-H. 1996 . Synth. Commun. , 26 : 3479
  • de Mattos , M. C.S. and Elias , S. M. 1995 . J. Braz. Chem. Soc. , 6 : 377 and references cited therein
  • Verghese , J. 1968 . Perfum. Essent. Oil Rec. , 59 : 439
  • de Mattos , M. C.S. , Kover , W. B. , Aznar , F. and Barluenga , J. 1992 . Tetrahedron Lett. , 33 : 4863
  • Weast , R. C. , ed. 1985 . “Handbook of Chemistry and Physics”, , 65th ed , C-361 Boca Raton : CRC Press .
  • The literature values of [α] for (R)-(+)-α-terpinyl chloride vary considerably (0,3a +39.5,8 +7512) and it should be mentioned that chiral analysis for determination of ee was not developed until recently. Our value of [α] for 84 % ee of (R)-(+)-α-terpinyl chloride would correspond to an absolute rotation13 of [α]max +74.2.
  • Von Braun , J. and Warner , G. 1929 . Chem. Ber. , 62 : 1056
  • Eliel , E. L. and Wilen , S. H. 1994 . “Stereochemistry of Organic Compounds” , 215 New York : John Wiley & Sons .
  • Our value of [α] for 60 % ee of (S)-(-)-α-terpinyl chloride would correspond to an absolute rotation13 of [α]max -73.5.

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