Phototranspositions of cyanothiophenes: permutation pattern analysis and the chemical trapping of an intermediate 5-thiabicyclo[2.1.0]pent-2-ene was written by Barltrop, John A.;Day, A. Colin;Irving, Edward. And the article was included in Journal of the Chemical Society, Chemical Communications in 1979.SDS of cas: 55406-13-8 This article mentions the following:
Through their first excited singlet states, cyanothiophenes undergo phototranspositions for which permutation pattern anal. and the isolation of furan-thiabicyclopentene adducts (from irradiation in furan), suggest a mechanism involving 2,5-bonding followed by a ‘walk’ of the S atom. E.g., irradiation of 3-cyanothiophene in furan gave 71 and 7% resp., of the 1:1 adducts I and II. This result provides evidence for the intermediate III, for which I and II are the expected Diels-Alder adducts with furan; a similar result occurred with 2-cyanothiophene. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8SDS of cas: 55406-13-8).
3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. SDS of cas: 55406-13-8
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts