Organic Lab Reactions 119

Organic Lab Reactions 119 - tetrahydro-3,4-benzpyrene 135...

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CHAPTER 4 THE FORMATION OF CYCLIC KETONES BY INTRAMOLECULAR ACYLATION WILLIAM S. JOHNSON The University of Wisconsin CONTENTS PAGE INTRODUCTION . . . , 115 THE SIZE OP THE RING 116 INFLUENCE OP THE'REACTIVITY OP THE AROMATIC NUCLEUS 118 Ortho and Para Directing Groups 118 Mela Directing Groups 120 Polycyclic Nuclei 122 STERIC FACTORS OTHER THAN RING SIZE 122 DIRECTION OP RING CLOSURE 124 The Benzene Nucleus 124 The Naphthalene Nucleus 125 The Phenanthrene Nucleus 126 Table I. Products of Cyclization in the Phenanthrene Series 127 METHODS OP CYCLIZATION . . > 130 The Friedel-Crafts Method 130 Table II. Cyclization of /3-Phenylpropionic Acid to Hydrindone-1 . . . 133 Table III. Cyclization of 7-Phenylbutyric Acid to Tetralone-1 134 Table IV. Cyclization of 7-3-Pyrenylbutyric Acid to 4'-Keto-l',2',3',4'-
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Unformatted text preview: tetrahydro-3,4-benzpyrene 135 Stannic Chloride 136 . With Phosphorus Pentachloride 136 Procedure I. l-Keto-l,2,3,4-tetrahydrophenanthrene 136 With Thionyl Chloride 137 Procedure II. l-Keto-l,2,3,4-tetrahydrophenanthrene 138 Table V. Comparison of Yields with Aluminum and Stannic Chloride in the Friedel-Crafts Method 140 Table VI. Cyclizations by the Friedel-Crafts Stannic Chloride Method . 141 Aluminum Chloride 144 With Phosphorus Pentachloride 145 Procedure III. 2-Phenyltetralone-l 145 With Thionyl Chloride * 146 Cyclization of Anhydrides . . . . 147 Table VII. Some Cyclizations by the Friedel-Crafts Aluminum Chloride Method 148 114...
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