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Updated: May 25, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
9-[(E)-2-(4,4,5,5-Tetra-methyl-1,3,2-dioxa-borolan-2-yl)ethen-yl]-9H-carbazole
Yuki Hatayama1, Tsunehisa Okuno
1Department of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan.
Abstract:
The title compound, C(20)H(22)BNO(2), is a simple olefinic compound which carries both B and N atoms that are trans to one another. The π-conjugated system of the compound is considered to be isoelectronic with 1,3-butadiene. There are two independent mol-ecules in the asymmetric unit in which the environments around the boron atoms are essentially planar (r.m.s. deviations of 0.0032 and 0.0021 Å for the BO(2)C planes). The dihedral angles of the olefinic planes with the boron planes are 5.70 (11) and 9.74 (9)°, respectively, while the dihedral angles of the olefinic planes with the carbazole planes are 19.37 (3) and 10.74 (6)°. These dihedral angles are consistent with those in 9-ethenylcarbazole and an ethenylboronic ester derivative. The N-Csp(2), B-Csp(2) and C=C bond lengths suggest that the contribution of the canonical structure can be described as N(+)=C-C=B(-).
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