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Title: Modern Friedel-Crafts Chemistry. Part 30­<sup>1 </sup>Facile synthesis of isomeric tri- and tetramethyltetrahydrophenanthrenes <i>via</i> rearranged cycloalkylation of suitably methylated 1-(1- and 2-naphthyl)-3-pentanols
Authors: Khalaf, Ali Ali
Albar, Hassan A
El-Fouty, Khalid O
Keywords: Friedel-Crafts cycloalkylation
carbocation rearrangements
1,1,2- and 3,4,4-trimethyltetrahydrophenanthrenes
1,1,2,2- and 3,3,4,4- tetramethyltetrahydrophenanthrenes
Issue Date: Feb-2010
Publisher: CSIR
Abstract: Facile methods for the synthesis of isomeric tri- and tetramethyl-tetrahydrophenanthrenes (<b>11, 18, 21,</b> and <b>27</b>) have been accomplished through rearranged Friedel-Crafts cycloalkylation of naphthylpentanols <b>1-4</b>, respectively. Thus, treatments with the mild 85% H<sub>2</sub>SO<sub>4</sub>, H<sub>3</sub>PO<sub>4</sub> and AlCl<sub>3</sub>/CH<sub>3</sub>NO<sub>2</sub> catalysts produced 1,1,2-trimethyl-1,2,3,4-tetrahydropenanthrene<b> 11</b> from 2,2-dimethyl-5-(1-naphthyl)-3-pentanol<b> 1</b>, 3,4,4-trimethyl-1,2,3,4-tetrahydrophenanthrene<b> 18</b> from 2,2-dimethyl-5-(2-naphthyl)-3-pentanol <b>2,</b> 1,1,2,2-tetramethyl-1,2,3,4-tetrahydrophenanthrene <b>21</b> from 2,2,3-trimethyl-5-(1-naphthyl)-3-pentanl <b>3</b> and 3,3,4,4-tetramethyl-1,2,3,4-tetrahydropenanthrene <b>27</b> from 2,2,3-trimethyl-5-(2-naphthyl)-3-pentanol <b>4</b>. Treatment with the strong AlCl<sub>3</sub> catalyst resulted in varying amounts of side products. The starting and final products were characterized by elemental analysis and IR, <sup>1</sup>H NMR and MS data.
Description: 203-208
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.49B(02) [February 2010]

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