In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called An enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction, published in 2019-01-25, which mentions a compound: 16400-32-1, mainly applied to nucleophilic substitution enantioselective thiocarboxylate tertiary bromide azide mechanism, Electric Literature of C5H7Br.
Bimol. nucleophilic substitution (SN2) plays a central role in organic chem. In the conventionally accepted mechanism, the nucleophile displaces a carbon-bound leaving group X, often a halogen, by attacking the carbon face opposite the C-X bond. A less common variant, the halogenophilic SN2X reaction, involves initial nucleophilic attack of the X group from the front and as such is less sensitive to backside steric hindrance. Herein, we report an enantioconvergent substitution reaction of activated tertiary bromides by thiocarboxylates or azides that, on the basis of exptl. and computational mechanistic studies, appears to proceed via the unusual SN2X pathway. The proposed electrophilic intermediates, benzoylsulfenyl bromide and bromine azide, were independently synthesized and shown to be effective.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics