Contrasteric stereochemical dictation of the cyclobutene ring-opening reaction by a vacant boron p orbital |
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| Authors: | Murakami Masahiro Usui Ippei Hasegawa Munehiro Matsuda Takanori |
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| Institution: | Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. murakami@sbchem.kyoto-u.ac.jp |
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| Abstract: | Cyclobutene, having a pinacolatoboryl group at the 3-position, was prepared by the reaction of trimethyl borate with a cyclobutenyl anion, which was generated by reductive lithiation of 3-(phenylselenyl)cyclobutene. Its thermal ring-opening reaction provided (Z)-1-borylbuta-1,3-diene selectively despite the arising steric congestion. The contrasteric behavior was accounted for by assuming an electron-accepting interaction of the vacant boron p orbital with the distorted breaking sigma orbital in the inward transition state. |
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