Preparative Organic Chemistry by G., and A. Martini, Editors; Hilgetag
By G., and A. Martini, Editors; Hilgetag
Xxv + 1,183 pages together with three appendices, index and errata, complete carbon processing and synthesis in three elements; development of equipment, chemical response and research of ensuing actual characters of carbon established elements, bw illustrations
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Additional info for Preparative Organic Chemistry
Amer. Chem. 109 From results to date, the following rules have been set up for these hydrogenations:161 1. Unsymmetrical double bonds, as in NO 2 , —N=C, ^>S=O, also —CEEEN, are hardly attacked at all, nor are bonds that are susceptible to other reducing agents. 110 Carbonyl groups are, however, reducible (see page 62). 2. trans-Otefins are reduced faster than cw-olefins. For example, under standard conditions fumaric acid reacts ten times as fast as maleic acid. 101 In some special cases these differences are so great as to control completely the course of the reaction, as-frans-frans-cyclododecatriene affords a mixture 111 of 95 % of cw-dodecene and 5 % of dodecane without a detectable trace of fraws-dodecene.
Chem. Soc, 74, 4449 (1952). 11 D. Papa, E. Schwenk, and E. Klingsberg, J. Amer. Chem. Soc, 73, 253 (1951); O. Neunhoeffer and H. Ulrich, Chem. , 88, 1123 (1955). 12 E. B. H. Waser and H. Mollering, Org. , 9, 84 (1929). 13 J. W. Robinson, /. Chem. Soc, 1949, 1855; M. D. Softer, R. A. Stewart, J. C. Cavagnol, H. E. Gellerson, and E, A. Bowler, /. Amer. Chem. Soc, 72, 3704 (1950). Addition of hydrogen to C = C bonds and aromatic systems 7 often recommended. For safety the reaction vessel should be placed on a sand-bath and not on a water-bath or Babo funnel.
112 F. Asinger et al, Chem. , 97, 1568 (1964). 113 J. W. Hamersma and E. I. Snyder, /. Org. , 30, 3985 (1965). 114 T. Kaufmann, C. Kosel, and W. Schoeneck, Chem. , 96, 999 (1963). Addition of hydrogen to C = C bonds and aromatic systems 17 not attack isolated double bonds, but fused aromatic rings are reduced, as are double bonds that are conjugated to aromatic rings. -distyrylbenzene. e. Other reducing agents Tin(n) chloride, phosphonium iodide, sodium dithionite, and hydrogen iodide were previously much used as reducing agents for carbon-carbon multiple bonds but are nowadays seldom of practical interest.