Related Experiment Video
Updated: May 14, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
Published on: March 25, 2017
1-Hydroxy-1H-benzo[d][1,2,6]oxazaborinin-4(3H)-one
Evan A Sarina1, Marilyn M Olmstead, Dung N Nguyen
1Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616-5292, USA.
Abstract:
The structure of the title compound, C(7)H(6)BNO(3), a new boron heterocycle, prepared by the condensation of (2-ethoxycarbonylphenyl)boronic acid and hydroxylamine, reveals the specific mode of intramolecular condensation between a phenylboronic acid and an ortho hydroxamic acid substituent. The crystal structure shows that dehydration occurs to form a planar oxazaborinine ring possessing both phenol-like B-O-H and lactam functional groups. In the extended structure, intermolecular hydrogen bonding generates a 14-membered ring. To our knowledge, this is the first crystal structure determination involving a six-membered ring that exhibits consecutive B-OH, O, NH, and C=O functional groups.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Reactions at the Benzylic Position: Oxidation and Reduction
Structure of Benzene: Molecular Orbital Model
Hydrolysis of Chlorobenzene to Phenol: Dow Process
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Structure of Benzene: Kekulé Model
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.