The proof of structure of 9-cyclohexylanthracene and the syntheses of 2',3' and 4'-methyl-2-(α-naphthylmethyl)-benzophenones and 2-(α-naphthylmethyl)-benzophenone

In 1947, while working on the aromatic cyclodehydration of ketones to their corresponding substituted anthracenes, Vingiello (1a) attempted to prepare 9-cyclohexylanthracene using this method. It was evident in the cyclization of o-benzylcyelohexyl-phenone (I) that the hydrol (II) postulated as an intermediate could lose water in two ways, yielding two different compounds 9,10-dihydro-9-cyclohexenylanthracene (IV) and 9-cyclohexyl-anthracene (III). This is shown in Chart I. Since a carbon, hydrogen analysis gives the same result for both compounds it is obvious that some other method of identification is necessary. It is the purpose of this part of the investigation to attempt to identify the existing structure by ultra-violet absorption analysis, and formation of derivatives and also to attempt to prepare 9-cyclohexylanthracene by an unequivocal method.

Name thesis:degree_name

Master of Science

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Polytechnic Institute

Year dc:date.issued

1950

Author dc:creator

• Shulman, Joe

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Language dc:language.iso

en_US

Handle dc:identifier.uri

http://hdl.handle.net/10919/52158

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/52158