Organic Lab Reactions 182

Organic Lab Reactions 182 - method 4S in benzene in...

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INFLUENCE OF METHOD ON DIRECTION OF CYCLIZATION 177 entation in intramolecular acylation are given by the cyclization of a,/3-dimethyl-7-2-naphthylbutyric acid 186 and of 7-2-anthrylbutyric acid. 89 In both reactions there .was a definite indication that some of the linear isomers were formed along with the normal products of ring closure. In the first this partial defiance of the normally strong tendency toward cyclization into the 1-position of the naphthalene nucleus seems to be significant. TABLE XIV CYCLIZATION OF -y-2-PHENANTHBYLBtrTYRic ACID Method of Cyclization 1. Friedel-Crafts—stannic chloride (thionyl chlo- ride) method m 2. Friedel-Crafts—stannic chloride (phosphorus pentachloride) meth- od 24 ° 3. Friedel-Crafts—alumi- t ' num chloride (phos- phorus pentachloride)
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Unformatted text preview: method 4S in benzene in nitrobenzene 4. 85% Sulfuric acid 4S 5. Acetic acid-anhydride with zinc chloride 4 * 3. Hydrogen fluoride 43 Yield of Total .L 1CXV4 \J1 J. \J LCvX Crude Ketone 74% (m.p. 122-124) 80% 91% (a) 70% (m.p. 90-110) 44% (m.p. 90-112) 62% 85% (m.p. 114-118) Yield of Benzan-thracene Ketone XCVII 14% . (m.p. 112-117) 35% (m.p. 115-116.5) 51% (m.p. 110-114) (6) 78% (m.p. 117-118) Yield of Chrysene Ketone XCVIII 74% (m.p. 122-124) '58% (m.p. 124-125)-17% (m.p. 122-125) 5% (m.p. 118-124) 23% (m.p. 123-125) 53% (m.p. 124-125) (a) Crude distilled neutral oil. (!>) All attempts to isolate any of XCVII failed. 2i " Fieser and Johnson, unpublished observation....
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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