Abstract
In the title compound, C15H15Br2NO2, two bridged tetra-hydro-furan rings adopt envelope conformations with the O atom as the flap. The pyrrolidine ring also adopts an envelope conformation with the spiro C atom as the flap. In the crystal, the mol-ecules are linked into dimers by pairs of C-H⋯O hydrogen bonds, thus generating R 2 2(18) rings. The crystal packing is dominated by H⋯H, Br⋯H, H⋯π and Br⋯π inter-actions. One of the Br atoms is disordered over two sites with occupation ratio of 0.833 (8):0.167 (8).
Highlights
H7AÁ Á ÁH14 Br1Á Á ÁBr1 H15CÁ Á ÁH10 H15BÁ Á ÁH11 Br2AÁ Á ÁH12 H5Á Á ÁC14 H13Á Á ÁO2
The crystal packing of the title compound is consolidated by C—HÁ Á ÁO hydrogen bonds (Table 1, Fig. 3) and C—HÁ Á Á and C—BrÁ Á Á interactions (Table 1, Fig. 4)
In order to present the intermolecular interactions in the crystal structure of the title compound in a visual manner, Hirshfeld surfaces (McKinnon et al, 2007) and their associated two-dimensional fingerprint plots (Spackman & McKinnon, 2002) were generated using CrystalExplorer17 (Turner et al, 2017)
Summary
The halogenation of oxabicycloheptenes plays an important role in the chemical transformations of bridged heterocycles because of the ability to carry out a complex transformation of the carbon skeleton in one step, which makes it possible to obtain products that are practically inaccessible in other ways from relatively simple starting compounds. Analysis of the literature data does not allow one to reliably predict the direction of the halogenation of oxabicycloheptenes. It can on the one hand be the halogen-initiated Wagner–Meerwein cationic rearrangement (Jung et al, 1985; Ciganek et al, 1995; Zubkov et al, 2004, 2018; Zaytsev et al, 2020), or on the other hand we can observe electrophilic addition of halogens to multiple bonds (Berson et al, 1954; Barlow et al, 1971; Kobayashi et al, 1976; Solov’eva et al, 1984). The different course of the halogenation reaction was shown to be anti-addition on the double bond with the formation of the title compound, 4,5-dibromo-6-methyl-2-phenylhexahydro3a,6-epoxy-isoindol-1(4H)-one, 2 (Fig. 1). The Br2 atom is disordered over two sites with occupation ratio of 0.833 (8):0.167 (8)
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