Current time in Korea 08:07 Apr 26 (Fri) Year 2024 KCS KCS Publications
KCS Publications
My Journal  Log In  Register
HOME > Search > Browsing(BKCS) > Archives

Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 19, Number 3
BKCSDE 19(3)
March 20, 1998 
 
Title
 Convenient Synthesis of Difurylmethanes and Dithienylmethanes and Their Application to the Syntheses of Core-Modified Porphyrins
Author
 Won-Seob Cho, Chang-Hee Lee*
Keywords
Abstract
 One flask synthesis of dithienylmethane and difurylmethane is reported. The reaction of aldehydes with excess furan or thiophene affords the meso-phenyldithienylmethane (DTM) and meso-phenyldifurylmethane (DFM), respectively. The reaction is catalyzed with trifluoroacetic acid or with BF3·O(Et)2. An acyl group is selectively introduced in 1 and 9 position of difurylmethane and dithienylmethane by use of an acid chloride and tin (IV) chloride. The reduction of resulting 1,9-bisacyldifurylmethane or 1,9-bisacyldithienylmethane affords the corresponding 1,9-bis-diol. An acid catalyzed condensation of diol with meso-phenyldipyrromethane followed by oxidation with DDQ gives the porphyrins. The reaction resulted meso-5,10,15,20-tetraphenyl-21,22-dithiaporphyrin (SSNN) or 15-mesityl-5,10,20-triphenyl-21,22-dioxaporphyrin (OONN), respectively. The formation of small amount of meso-tetraphenylporphyrin (TPPH2) is also observed. The formation of TPP indicates that meso-phenyldipyrromethane is reversibly cleaved and form pyrrole and pyrrylbenzylcarbocation during the condensation. The proton nmr and electronic spectrum of the SSNN and OONN porphyrins are somewhat different from the previously synthesized meso-5,10,15,20-tetraphenyl-21,23-dithiaporphyrin (SNSN) or meso-5,10,15,20-tetraphenyl-21,23-dioxaporphyrin (ONON).
Page
 314 - 319
Full Text
 PDF

How to access to the WOL for The Bulletin of the Korean Chemical Society ?

The Bulletin of the Korean Chemical Society will be co-published with Wiley-VCH from 2015 towards. The online version of the Journal will thus be available on Wiley Online Library, Wiley(-VCH)'s global online platform.

KCS members can get a free online access to the Bulletin of the Korean Chemical Society in WOL.

Close