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Updated: May 27, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2-Azido-methyl-3-methyl-1-phenyl-sulfonyl-1H-indole
Abstract:
In the title compound, C(16)H(14)N(4)O(2)S, the plane of the indole ring is twisted by 70.4 (2)° with respect to the plane of the azidomethyl- substituent. As a result of the electron-withdrawing character of the phenyl-sulfonyl groups, the N-C bond lengths are slightly longer than the anti-cipated value of approximately 1.355 Å for an N atom with a planar configuration. The indole ring is essentially planar, with a maximum deviation of 0.0296 Å. The azide group is almost linear, the N-N-N angle being 171.4 (3)°. The methyl group on the azide-substituted C atom is in a flagpole position. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 87.07 (10)° with the best plane of the indole moiety. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions, which link the mol-ecules into infinite chains running parallel to the b axis. The crystal packing is further stabilized by C-H⋯π inter-actions.
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