Abstract
The relative stereo- and regiochemistry of the racemic title compound, C25H19NO7, were established from the crystal structure. The fused benzene ring forms dihedral angles of 77.3 (1) and 60.3 (1)° with the hy-droxy-substituted benzene ring and the nitro-substituted benzene ring, respectively. The dihedral angle between the hy-droxy-substituted benzene ring and the nitro-substituted benzene ring is 76.4 (1)°. An intra-molecular O-H⋯O hydrogen bond closes an S(6) ring. In the crystal, weak C-H⋯O hydrogen bonds connect the mol-ecules, forming layers parallel to (100). Within these layers, there are weak π-π stacking inter-actions with a ring centroid-ring centroid distance of 3.555 (1) Å.
Highlights
The relative stereo- and regiochemistry of the racemic title compound, C25H19NO7, were established from the crystal structure
We set out to determine the effect of C1 substitution on controlling the regioselectivity in the iridium-catalysed hydroacylation reaction with salicylaldehyde II on unsymmetrical oxabenzonorbornadienes
0.036, 0.093, 1.01 4727 302 H atoms treated by a mixture of independent and constrained refinement 0.25, À0.21
Summary
Our research group (Ballantine et al, 2009; Edmunds et al, 2015; Hill & Tam, 2019; Edmunds et al, 2016; Raheem et al, 2014) has investigated the effects of various C1-substituted oxabenzonorbornadienes (OBD) on controlling the regioselectivity of ring-opening reactions. In 2015, Nagamoto and Nishimura reported the iridiumcatalysed hydroacylation reaction of bicyclic alkenes with 2-hydroxybenzaldehyde and its derivatives. Based upon these findings, we set out to determine the effect of C1 substitution on controlling the regioselectivity in the iridium-catalysed hydroacylation reaction with salicylaldehyde II (see Fig. 1) on unsymmetrical oxabenzonorbornadienes.
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