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The Formation of Cyclic Ketones by Intramolecular Acylation

  1. William S. Johnson

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or002.04

Organic Reactions

Organic Reactions

How to Cite

Johnson, W. S. 2011. The Formation of Cyclic Ketones by Intramolecular Acylation. Organic Reactions. 2:4:114–177.

Author Information

  1. The University of Wisconsin

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

The cyclizations of gamma-phenylbutyric acid (I) to tetralone-1 (II) and of beta-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, Such ring closures have been effected by a variety of methods, generally involving either the direct cyclodehydration of the acids or the cyclodehydrohalogenation of the acid chlorides by an intramolecular Freidel-Crafts reaction. This chapter presents a discussion of these methods and the various problems involved in the formation of cyclic ketones by the ring closure of aryl-substituted aliphatic acid.

Keywords:

  • cyclic ketones;
  • intramolecular acylation;
  • ring size;
  • steric factors;
  • ring closures;
  • benzene;
  • naphthalene;
  • phenathrene;
  • cyclization