Repozytorium
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Kolekcje
Inne
Protection/Deprotection-Free Syntheses and Structural Analysis of (Keto-aryl)diynes.
Autorzy
Rok wydania
2008
Czasopismo
European Journal of Organic Chemistry
Strony
4598-4606
DOI
10.1002/ejoc.200800350
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The reactions of precursors 4-BrC6H4COR with TMSCCH (Sonogashira coupling) followed by in situ deprotection and
subsequent dimerization gave thermally stable dimeric ketodiynes RCOC6H4(CC)2C6H4COR (8–11) as yellow powders
in 25–85% yields without the necessity of carbonyl group protection/deprotection steps. Compounds 8–11 were also
synthesized by an alternative method that utilized α-haloalkynes previously obtained directly from TMS-protected 4-
RCOC6H4CCTMS alkynes. The resulting diynes were characterized by spectroscopic methods and in most cases by X-ray crystallography. Careful analysis of the crystal data revealed a surprisingly high degree of chain curvature. Moreover, compounds 9 (R = Me) and 10 (R = Et) were extremely flat, which greatly facilitates electronic communication throughout the whole molecule. Deeper analysis of the
packing motifs showed 9 to have a great potential for topochemical 1,4-polymerization.
Słowa kluczowe
Polyynes, Homocoupling, Dimerization, Halogenation, Alkynes
Adres publiczny
https://doi.org/10.1002/ejoc.200800350
Strona internetowa wydawcy
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