Abstract
The title compound, C10H7NO2S, provides the first structure of an α-alkenyl oxa-thia-zolone ring. The phenyl ring and the oxa-thia-zolone groups make dihedral angles of 0.3 (3) and -2.8 (3)°, respectively, with the plane of the central alkene group; the dihedral angle between the rings is 2.68 (8)°. A careful consideration of bond lengths provides insight into the electronic structure and reactivity of the title compound. In the crystal, extended π-stacking is observed parallel to the a-axis direction, consisting of cofacial head-to-tail dimeric units [centroid-centroid distance of 3.6191 (11) Å]. These dimeric units are separated by a slightly longer centroid-centroid distance of 3.8383 (12) Å, generating infinite stacks of mol-ecules.
Highlights
We have focused our student projects on the preparation, characterization and chemistry of oxathiazolone derivatives
The preparations of oxathiazolone derivatives use methods developed in earlier laboratories and allow for subsequent chemistry of either the heterocycle or substituent group, which can be explored in a three-to-four week project cycle individually, in groups and in inquiry-based class projects
Derivatives of the oxathiazolone heterocycle have been known since their first preparation in 1967 by Muhlbauer and
Summary
A common feature of the undergraduate organic chemistry teaching laboratory is the capstone, multi-step synthetic project that allows the student to integrate their lecture and laboratory experiences and capture a glimpse of research chemistry (Christiansen et al, 2014). The title compound was first prepared from cinnamyl amide by Paton and coworkers (Paton et al, 1983) and the synthesis was subsequently reported in a patent for use as modulating agents for amino acid receptors (Cosford et al, 2005). Our interest in this derivative of the oxathiazolone heterocycle was initially focused on the potential for exploring the chemistry of the alkene moiety in the styryl group for subsequent assessment of the substituent effect of the oxathiazolone on the alkene addition and electrophilic substitution chemistry
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