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Extra resources for Advanced Organic Synthesis. Methods and techniques
Friederang and D. S. Tarbell, /. Org. Chem. 33, 3797 (1968). G. A. Wiley, R. L. Hershkowitz, B. M. Rein, and B. C. Chung, /. Amer. Chem. Soc. 86,964 (1964). D. Levy and R. Stevenson, J. Org. Chem. 30, 3469 (1965). J. P. Schaefer, J. G. Higgins, and P. K. Shenov, Org. Syn. 48, 51 (1968). REFERENCES 53 7. C. Djerassi, Chem. Rev. 43, 271 (1948); L. Horner and E. H. Winkelmann in "Newer Methods of Preparative Organic Chemistry" ( W. ), Vol. 3, Academic Press, New York, 1964. 8. N. S. Isaacs, "Experiments in Physical Organic Chemistry," p.
The generation and use of the reagent are described in the procedures. 36 4. HYDROBORATION A. n-OCTANAL FROM 1-OCTYNE (J) (CH3)2C=CHCH3 B2H6 > (iso-C 5 H n ) 2 BH C6H13C=CH +(ISo-C 5 Hn) 2 BH -* C6H13-CH=CH-B(iso-C5Hn)2 2 2 > NaOH «-C 7 H, 5 —CHO + iso-C 5 H n —OH A 500-mI three-necked flask is fitted with a condenser, a pressure-equalizing dropping funnel, a magnetic stirrer, and a thermometer. 48 mole) of 2-methyl-2-butene and 180 ml of a 1 M solution of sodium borohydride in diglyme. The flask is cooled in an ice bath and stirring begun.
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. S. Noyce, B. N. Bastian, P.
Advanced Organic Synthesis. Methods and techniques by Richard S. Monson