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Organic Lab Reactions 123

Organic Lab Reactions 123 - adipic acid(XVII which was...

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118 THE FORMATION OP CYCLIC KETONES COjH Hj—CH—(CH 2 )r-V^ XIII CO 2 H (CH 2 ) 3 C,H 6 CH 2 CH 2 CO 2 H (CH 2 ) 2 CO 2 H XVIII Proof of the premise was found in the cyclization 7 of a-benzyl-5-phenyl- valeric acid (XIII) and of a-benzylglutaric acid (XV) which gave the hydrindone derivatives XIV and XVI, respectively, and none of the isomeric benzosuberones. The formation of 4-phenylhydrindone-l from j3-2-biphenylpropionic acid afforded further substantiation, since the acid has the structural possibility of cyclizing to a seven-membered ring ketone. ' The formation of a six- in preference to a seven-membered ring follows as a corollary from the above considerations. Experimental foundation, moreover, was afforded by examination of the ring closure of /3-benzyl-
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Unformatted text preview: adipic acid (XVII), which was found to yield only the tetfalone deriva-tive XVIII. 11 No examples have been found in which either an eight-membered ring or a four- or three-membered ring has been fbrmed by intramolecular acylation. The failure of phenylacetyl chloride and benzoyl chloride to cyclize under the conditions of the Friedel-Craf ts reaction has been reported. 12 INFLUENCE OF THE REACTIVITY OF THE AROMATIC NUCLEUS Ortho and Para Directing Groups. In general the common rules of orientation regarding intermoleoular acylation can be extended to the 11 v. Braun, Bayer, and Caasel, Ber., 60, 2602 (1927). 1J Wedekind, Ann., 323, 246 (1902)....
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