The preparation of substituted bithiophenyl aldehydes via the ring opening of dithieno[2,3-b:3′,2′-d]thiophene in the presence of n-BuLi

Add time:09/30/2019    Source:infona.pl

In the presence of n-BuLi in THF at low temperature, the phenomena of ring opening of symmetric substituted dithieno[2,3-b:3′,2′-d]thiophenes were observed. After quenching the organolithium intermediates with dry DMF, a series of substituted novel bithiophenyl aldehydes were prepared in good to excellent yields. The mechanism shows the key step for the ring opening of dithieno[2,3-b:3′,2′-d]thiophene is the nucleophilic attack of butyl anion onto the sulfur atom of the central ring. Total ten samples of symmetric substituted dithieno[2,3-b:3′,2′-d]thiophenes and their ring-opened products, the substituted bithiophenyl aldehydes were characterized by 1 H NMR, 13 C NMR, and HRMS. Two ring-opened products were confirmed by X-ray single crystal analysis.

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