1,3‐Dihydro‐1‐hydroxy‐3‐morpholin‐4‐yl‐2,1‐benzoxaborole: product of the reaction of o‐formylphenylboronic acid with morpholine

Abstract

o-Formylphenylboronic acid reacts with morpholine to form 1,3-dihydro-1-hydroxy-3-morpholin-4-yl-2,1-benzoxaborole. The typical hydrogen-bonded dimer motif with a planar benzoxaborole fragment has been obtained in the solid state.

Lewis acidity and sugar receptor activity of 3-amino-substituted benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues

“…The morpholine ring shows the chair conformation with nitrogen and oxygen atoms lying on opposite sides of the ring. The similar conformation of the morpholine ring was observed in acid (3a) 46 and benzoxaborole (2a) 23 analogues. Moreover, the morpholine nitrogen atom serves as a donor to the 20 methoxy oxygen atom, O4, forming the intramolecular hydrogen bond described with the graph S (7).…”

Benzoxaboroles – Old compounds with new applications

“…This lengthening has been attributed to the steric effect of the morpholine fragment. The planes of morpholinyl groups are perpendicular to the planes of the central dimer ring, however, no other hydrogen bonds are observed with substituent atoms able to act as a hydrogen acceptor [23].…”

“…This can be deduced from the ranges of geometric parameters: the exocyclic BO bond changes in the range 1 [23], respectively. Importantly, these differences are not only the consequence of the electronic structure of the substituents, but also due to the intermolecular interactions in the crystal lattice [14,23].…”

Efficient Fractionation of Spruce by SO2‐Ethanol‐Water Treatment: Closed Mass Balances for Carbohydrates and Sulfur

“…There are only a few molecular structures of benzoxaboroles described in the literature. Therefore, we would like to present spectroscopic and computational findings for two modified benzoxaborole rings of 1,3‐dihydro‐1‐hydroxy‐3‐(morpholin‐ 4‐yl)‐2,1‐benzoxaborole20 ( IIa ) and 1,3‐dihydro‐1‐hydroxy‐2,1‐ benzoxaborole19 ( IIb ). The latter one serves as a reference structure of the benzoxaborole family.…”

“…The latter one serves as a reference structure of the benzoxaborole family. Benzoxaborole with morpholinyl substituent ( IIa ) reveals interesting crystal packing due to the presence of morpholinyl rings 20. The morpholinyl substituent is responsible for steric effects and further for the intermolecular hydrogen bond lengthening.…”