Work

Photochemical and Photophysical Behavior of p -Methoxyphenyl alkenyl Phenanthrenecarboxylates. I. Structure and Competitive Formation of Intramolecular Cycloaddition Products

Year: 1990

Type: article

Abstract: Irradiation of (E)-3-(p-methoxyphenyl)-3-pentenyl, (E)-4-(p-methoxyphenyl)-4-hexenyl, and (E)-5-(p-methoxyphenyl)-5-heptenyl 9-phenanthrenecarboxylates (B-2E, B-3E, and B-4E, respectively) in benzene gave intramolecular [2+2] cycloadducts, cyclobutane derivatives (CB-2, CB-3, and CB-4, respectively) possessing the same conformation as an intermolecular [2+2] cycloadduct (CB-0) between methyl 9-phenanthrenecarboxylate (9-MCP) and trans-anethole (t-AN), and oxetane derivatives (OX-2, OX-3, and OX-4, respectively) arising from intramolecular cycloaddition between the carbonyl group and the olefinic double bond. However, (E)-4-(p-methoxyphenyl)-3-butenyl and (E)-5-(p-methoxyphenyl)-4-pentenyl 9-phenanthrenecarboxylates (A-2E and A-3E, respectively) afforded only products derived from oxetane precursors.

Source: Bulletin of the Chemical Society of Japan

DOI: 10.1246/bcsj.63.1049

Authors: Hirochika Sakuragi, Katsumi Tokumaru, Hiroki Itoh, Kohki Terakawa, Katsuo Kikuchi, R A Caldwell, Chien-Chung Hsu

Institutions: University of Tsukuba, Yamagata University, The University of Texas at Dallas

Language: English

Topic: Organic Chemistry Cycloaddition Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

OpenAlex ID: W2139330158

FWCI: 4.409

Cites: 26

Cited by: 26

Related to: 10