New PDF release: Advanced Organic Synthesis

By Richard S. Monson

ISBN-10: 0125049501

ISBN-13: 9780125049504

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Example text

Halides from Alcohols and Phenols by Triphenylphosphine Dihalide A halogenating system related to the preceding case is formed by the reaction of triphenylphosphine with molecular bromine or chlorine. The system is not as sensitive to moisture as the phosphine-carbon tetrahalide system (see preceding section), but it suffers from the disadvantage that hydrohalic acids are produced as the reaction proceeds. Nevertheless, sensitive compounds can be successfully halogenated by the system, as exemplified by the preparation of cinnamyl bromide from the alcohol.

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30, 3206 (1965). 4. D. S. Noyce, G. L. Woo, and B. R. Thomas, /. Org. Chem. 25, 260 (1960). 5. W. M. Pearlman, Org. Syn. 49, 75 (1969). 6. J. A. Osborn, F. H. Jardine, J. F. Young, and G. Wilkinson, /. Chem. Soc. (A)1 p. 1711 (1966). 7. A. J. Birch and K. A. M. Walker, /. Chem. Soc. (C), p. 1894 (1966). 8. J. A. Osborn and G. Wilkinson, Inorg. Syn. 10, 67 (1967). 9. C. Djerassi and J. Gutzwiller, /. Amer. Chem. Soc. 88, 4537 (1966). 10. A. J. Birch and K. A. M. , p. 3457 (1967). The Introduction of Halogen The introduction of halogen into organic molecules can be carried out by a variety of addition or substitution reactions.

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Advanced Organic Synthesis by Richard S. Monson


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