Stereospecific and Stereoselective Reactions. I. Preparation of Amines from Alcohols

Journal of the American Chemical Society

Volumn 94, Issue 2, 1972, Pages 679-680

  Mitsunobu, Oyo ^a   Wada, Makoto ^a   Sano, Takashi ^a  

^a AOYAMA GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947090431     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00757a085     Document Type: Letter

References (18)

1. Houben-Weyl, “Methoden der Organischen Chemie,” Vol. XI, Part 1, Georg Thieme Verlag, Stuttgart, 1957;
2. S. R. Sandler and W. Kars, “Organic Functional Group Preparation,” Academic Press, New York, N. Y., 1968;
3. C. A. Buehler and D. E. Pearson, “Survey of Organic Syntheses,” Wiley-Interscience, New York, N. Y., 1970.
4. Streitwieser and Schaeffer have demonstrated that the direct displacement reaction of sulfonate esters with azide ion proceeds with nearly complete inversion: A. Streitwieser, Jr., and W. D. Schaeffer, J. Amer. Chem. Soc., 78, 5597 (1956).
5. E. H. White and C. A. Elliger, J. Amer. Chem. Soc., 87, 5261 (1965), and references therein.
6. E. M. Burgess, H. R. Penton, Jr., and E. A. Taylor, J. Amer. Chem. Soc., 92, 5224 (1970).
7. O. Mitsunobu and M. Yamada, Bull. Chem. Soc. Jap., 40, 2380 (1967);
8. O. Mitsunobu, K. Kato, and J. Kimura, J. Amer. Chem. Soc., 91, 6510 (1969);
9. O. Mitsunobu and M. Eguchi, Bull. Chem. Soc. Jap., 44, 3427 (1971);
10. O. Mitsunobu, J. Kimura, and Y. Fujisawa, Bull. Chem. Soc. Jap., in press.
11. R. G. Harvey and E. R. De Sombre, Top. Phosphorus Chem., 1, 57 (1964);
12. R. F. Hudson, “Structure and Mechanism in Organo-phosphorus Chemistry,” Academic Press, New York, N. Y., 1965;
13. A. J. Kirby and S. G. Warren, “The Organic Chemistry of Phosphorus,” Elsevier, Amsterdam, 1967.
14. W. Gerrard and W. J. Green, J. Chem. Soc., 2550 (1951).
15. R. G. Weiss and E. I. Snyder, J. Org. Chem., 35, 1627 (1970); and references therein.
16. A. W. Ingersoll, “Organic Reactions,” Vol. 2, R. Adams, Ed., Wiley, New York, N. Y., 1960, p 376. Optical rotations were measured with a JASCO ORD/UV-5.
17. 3). The specific rotatory power increases with dilution until a concentration of about 3 % is reached, where it becomes constan., Thus, our (S)-(+)-2-octanol was about 100% optical purity (J. Chem. Soc., 2953 (1953)).
18. The recorded molecular rotation of (+)-2-octylamine is [M]d 8.50° (in 5.953 % benzene solution) which corresponds to [a]D + 6.59°: F. G. Mann and J. W. G. Porter, J. Chem. Soc., 456 (1944).