J 2000

Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes

DREHER, Spencer, Kamil PARUCH and Thomas KATZ

Basic information

Original name

Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes

Name in Czech

Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes

Authors

DREHER, Spencer (840 United States of America), Kamil PARUCH (203 Czech Republic, guarantor) and Thomas KATZ (840 United States of America)

Edition

Journal of Organic Chemistry, 2000, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 3.689

RIV identification code

RIV/00216224:14310/00:00036036

Organization unit

Faculty of Science

Keywords (in Czech)

helicene; alkoxyl; diastereomer; separation

Keywords in English

helicene; alkoxyl; diastereomer; separation

Tags

Změněno: 25/6/2009 15:21, doc. Mgr. Kamil Paruch, Ph.D.

Abstract

ORIG CZ

V originále

Alcs. contg. HCl transform the hydroquinone redn.-products of helicenebisquinones into p-alkoxyphenols that have the alkoxyls specifically on the peripheries of the helixes. The reactions are quick, and the yields are high. Alkoxyls at the 6-position are replaced also, but only after 2 h at 60 C, not after the 5 min at 25 C sufficient to replace the peripheral hydroxyls of the hydroquinones. After the remaining inside hydroxyls of a dihydroxytetramethoxy[6]helicene prepd. by this procedure were converted into camphanates, one diastereomer crystallizes from soln., allowing an enantiomer resoln. to be carried out on a large scale. By then simply re-applying the procedure with alc. acid, a variety of resolved dihydroxytetraalkoxy[6]helicenes can be prepd. in excellent yields without resoln. procedures having to be developed for each. Similar procedures are effective when applied to a [7]carbohelicene.

In Czech

viz Anotace