Abstract
AbstractThe attempted syntheses of 3,4‐dimethylborole derivatives further bearing bulky SiMe2t‐Bu groups in 2,5‐position are reported. Isolation of base‐stabilized adducts to the chloroborole were achieved. The respective free borole was found to be unstable and revealed 1,3‐hydrogen atom shift isomerization to a 1‐bora‐1,3‐butadiene with an s‐trans orientation and lacking cyclic conjugation of the π‐system. Computational probing indicates elevated C−H acidity of methyl groups attached to the butadiene backbone in boroles, exceeding the C−H acidity of respective boron‐bound methyl groups. Derivatization attempts of the new chloroborole are reported.
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