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Palladium-catalyzed carbonylation of 2-butyne-1,4-diol derivatives: formation of fulgide or lactone

✍ Scribed by Jitsuo Kiji; Yuuichi Kondou; Masahiro Asahara; Yasushi Yokoyama; Toshiya Sagisaka

Book ID: 104422265
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 90 KB
Volume: 197
Category: Article
ISSN: 1381-1169
DOI: 10.1016/s1381-1169(02)00659-3

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✦ Synopsis

The carbonylation of the substituted 2-butyne-1,4-diols, RArC(OH)≡C(OH)ArR (Ar, 2,5-dimethylthienyl; R, alkyl) was studied by using Pd(OAc) 2 /I 2 as the catalyst in benzene under pressure. The diols bearing methyl or isopropyl group as the alkyl substituent gave photochromic fulgide (4a or 4b). On the other hand, the carbonylation of the diol bearing bulky t-butyl group did not afford the corresponding fulgide but lactone 5, together with butatriene 6.

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