Methyl 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-nitrobenzoate

S F Jenkinson,M I Simone,A L Thompson

doi:10.1107/s1600536812029650

Abstract

The six-membered boronate ester ring of the title compound, C13H16BNO6, adopts an envelope conformation with the C atom bearing the dimethyl substituents at the flap. The O—B—C—C torsion angles between the boronate group and the benzene ring are 72.5 (2) and 81.0 (2)°. The 4-nitrobenzoate unit adopts a slightly twisted conformation, with dihedral angles between the benzene ring and the nitrate and methyl ester groups of 17.5 (2) and 14.4 (3)°, respectively. In the crystal, inversion-related pairs of molecules show weak π–π stacking interactions [centroid–centroid distance = 4.0585 (9) Å and interplanar spacing = 3.6254 (7) Å].

Highlights

The six-membered boronate ester ring of the title compound, C13H16BNO6, adopts an envelope conformation with the C atom bearing the dimethyl substituents at the flap
The synthesis of ortho-substituted aromatic esters becomes increasingly difficult as the aromatic ring becomes more substituted (Baudoin et al, 2000; Fang et al, 2005; Ishiyama et al, 2010; Wang et al, 2006)
The purification of the boronate ester 2 was difficult because the bis(neopentyl glycolato)diboron reagent, which was used in excess, proved difficult to completely remove via a variety of purification techniques

Summary

Introduction

The six-membered boronate ester ring of the title compound, C13H16BNO6, adopts an envelope conformation with the C atom bearing the dimethyl substituents at the flap. Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al, 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al, 2003); molecular graphics: CAMERON (Watkin et al, 1996); software used to prepare material for publication: CRYSTALS and PLATON (Spek, 2009).

Results

Conclusion