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By Richard S. Monson

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During this quantity, these practical teams containing heteroatoms that experience received significance in natural synthesis are handled intimately. The creation of those quite a few teams and their suitable changes are defined and a number of the points of chemoselectivity, regioselectivity and stereoselectivity are mentioned.

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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. The classical methods for the addition of halogen to double bonds or the substitution of halogen for hydroxyl by hydrohalic acids are too well known to bear repetition here. Discussed below, then, are methods that are of interest because of their stereospecific outcome or because they may be used on sensitive substrates. I. Halides from Alcohols by Triphenylphosphine-Carbon Tetrahalide Triphenylphosphine in refluxing carbon tetrachloride converts primary and secondary alcohols into the corresponding chlorides under very mild conditions (I) with inversion of configuration (2, 3).

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. The classical methods for the addition of halogen to double bonds or the substitution of halogen for hydroxyl by hydrohalic acids are too well known to bear repetition here. Discussed below, then, are methods that are of interest because of their stereospecific outcome or because they may be used on sensitive substrates.

4. J1(9)-Octalone-2-gives trans-2-decalone, bp 112-114°/13 mm. V. -unsaturated y-diketones can conveniently be done with zinc in acetic acid. The following procedure is applicable to the reduction of the Diels-Alder adduct of quinone and butadiene (Chapter 8, Section II). C/s-J2-5,8-OCTALINDIONE (8) O Zn/HOAc 30 3. DISSOLVING METAL REDUCTIONS Six grams of the quinone-butadiene adduct are dissolved in 25 ml of 95% acetic acid and the solution is placed in a round-bottom flask fitted with a thermometer and a mechanical stirrer.

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Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson


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