NEW SYNTHESES OF CYCLOPENTA[CD]PYRENE 3,4-OXIDE AND 4-PYRENYLACETIC ACID

被引：9

作者：

SAHALI, Y ^{[1
]}

SKIPPER, PL ^{[1
]}

TANNENBAUM, SR ^{[1
]}

机构：

[1] MIT,DIV TOXICOL,CAMBRIDGE,MA 02139

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 09期

关键词：

D O I：

10.1021/jo00296a065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New syntheses of cyclopenta[cci]pyrene 3,4-oxide (CPPE) and 4-pyrenylacetic acid, a key intermediate in the synthesis of cyclopenta[cd]pyrene and CPPE, are described starting from 1,2,3,6,7,8-hexahydropyrene. 4-Pyrenylacetic acid is prepared from the corresponding alcohol, 2-(4-pyrenyl)ethanol, by applying two mild oxidation reactions. 4-Pyrenylacetaldehyde was obtained by N-chlorosuccinimide dimethyl sulfide oxidation, and this was converted smoothly to the desired 4-pyrenylacetic acid by silver oxide oxidation, an approach that has potential for a new route to arylacetic acids from arylethanols. The epoxide CPPE is prepared by cyclization of the 3,4-frans-dihydroxycyclopenta[cd]pyrene via its monotosylate, prepared in situ, with powdered sodium hydroxide. © 1990, American Chemical Society. All rights reserved.

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页码：2918 / 2920

页数：3

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