Unexpected product in the synthesis of bis(2-iodo-3-thienyl)methanol: Characterisation of bis[bis(2-iodo-3-thienyl)methyl]ether

Abstract

Following a literature procedure for the preparation of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one, it was found that insufficient attention and control of the reaction temperature led to the formation of bis[bis(2-iodo-3-thienyl)methyl]ether, via a yet to be determined mechanism. Though the synthetic route to the desired ketone has previously been extensively investigated, and numerous byproducts isolated and characterised, this coupled ether product has not been previously reported nor foreseen. Presented herein are the synthesis and full characterisation of the new ether compound. © Georg Thieme Verlag Stuttgart.