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Soc. 81, 5405 (1959). 11. H. O. House and H. W. Thompson, /. Org. Chem. 28, 360 (1963). 12. H. O. House and R. W. Bashe, /. Org. Chem. 30, 2942 (1965). 13. A. Butenandt and A. WoIfT, Chem. Ber. 68B, 2091 (1935). 14. M. Yanagita and K. Yamakawa, /. Org. Chem. 21, 500 (1956). 15. G. F. H. Green and A. G. Long, /. Chem. , p. 2532 (1961). 16. E. A. Fehnel, S. Goodyear, and J. Berkowitz, /. Amer. Chem. Soc. 73, 4978 (1951). 17. E. L. Bennett and C. Niemann, /. Amer. Chem. Soc. 74, 5076 (1952). 18. D.

Normant, and B. Tchoubar, Bull. Soc. Chim. , p. 595 (1968). 8. E. E. van Tamelen, M. Shamma, A. W. Burgstahler, J. Wolinsky, R. Tamm, and P. E. Aldrich, /. Amer. Chem. Soc. 91, 7315 (1969). 9. W. Huckel and W. Kraus, Chem. Ber. 92, 1158 (1959). Hydroboration A remarkable variation of the hydride reduction is the addition to double bonds of diborane (B2H6) (7). Easily generated by the reaction of boron trifluoride etherate with sodium borohydride, the reagent may be used in the generating solution or may be distilled into a receiving flask containing an ether as solvent.

5-5 g (75-83%). The product may be recrystallized from petroleum ether yielding material with a reported (9) mp of 106°. REFERENCES 1. A. J. Birch, Quart. Rev. 4, 69 (1950); A. J. Birch and H. Smith, Quart. Rev. 12, 17 (1958). 2. R. A. Benkeser and E. M. Kaiser, /. Org. Chem. 29, 955 (1964). 3. L. Reggel, R. A. Friedel, and I. Wender,/. Org. Chem. 22, 891 (1957); W. G. Dauben, E. C. Martin, and G. J. Fonken, J. Org. Chem. 23, 1205 (1958). 4. G. Stork and S. D. Darling, /. Amer. Chem. Soc. 86, 1761 (1964) and references cited therein.

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