Organic Lab Reactions 120

Organic Lab Reactions 120 - Table XIV. Cydization of...

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INTRODUCTION 115 PAGE The Hydrogen Fluoride Method 157 General Procedure 158 Procedure IV. 8-Keto-3,4,5,6,7,8-hexahydro-l,2-benzanthracene ... . 158 Table VIII. Cyclizations with Hydrogen Fluoride 160 The Sulf uric Acid Method 162 Procedure V. Ring Closure with Sulfuric Acid 164 Table IX. Comparison of Yields Obtained by the Sulfuric Acid and Friedel- Crafts Methods 165 Table X. Some Cyclizations with Sulfuric Acid 166 Other Methods 169 'Stannic Chloride on the Free Acid 169 Phosphorus Pentoxide 170 Miscellaneous Methods and Reagents 170 Table XI. Some Cyclizations with Stannic Chloride on the Free Acids . . 172 Table XII . Some Cyclizations with Phosphorus Pentoxide ... . 173 Table XIII. Some Cyclizations by Heating the Free Acid Chlorides . . 174 TH E INFLTTENCE OF THE METHOD ON THE DIBECTION OF CYCLIZATION ... . 174
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Unformatted text preview: Table XIV. Cydization of 7-2-Phenanthrylbutyric Acid . 1 7 7 INTRODUCTION The cyclizations of 7-phenylbutyric acid (I) to tetralone-1 (II) and of . /3-phenylpropionic acid (III) to hydrindone-1 (IV) exemplify a type of intramolecular acylation which has served as an important tool in the synthesis of polycyclic hydroaromatic and aromatic compounds. 1-2> 3 Such ring closures have been effected by a variety of methods generally involving either the direct cyclodehydration of the acids or the cyclo-dehydrohalogenation of the acid chlorides by an intramolecular Friedel-1 Linetead, Ann. Repta. Chem. Soc., 33, 336 (1936). 2 Springall, Ann. Repts. Chem. Soc., 36, 301 (1939). 8 Fieser, "Chemistry of Natural Products Related to Phenanthrene," 2nd ed., Eeinhold Publishing Corp., 1937....
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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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