Home / Publications / Wedekind–Fock–Havinga salt Me(Et)N+(All)PhI–·CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration

Wedekind–Fock–Havinga salt Me(Et)N+(All)PhI–·CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration

Remir Grigorevich Kostyanovsky 1
Remir Grigorevich Kostyanovsky
, 
Vasily Remirovich Kostyanovsky 1
Vasily Remirovich Kostyanovsky
, 
Gulnara Konstantinovna Kadorkina 1
Gulnara Konstantinovna Kadorkina
, 
Konstantin Alexandrovich Lyssenko 2
Konstantin Alexandrovich Lyssenko
10.1070/MC2001v011n01ABEH001420
Published 2001-02-22
Communication , Volume 11, Issue 1, 1-5
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Kostyanovsky R. G. et al. Wedekind–Fock–Havinga salt Me(Et)N+(All)PhI–·CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration // Mendeleev Communications. 2001. Vol. 11. No. 1. pp. 1-5.
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Kostyanovsky R. G., Kostyanovsky V. R., Kadorkina G. K., Lyssenko K. A. Wedekind–Fock–Havinga salt Me(Et)N+(All)PhI–·CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration // Mendeleev Communications. 2001. Vol. 11. No. 1. pp. 1-5.
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TY - JOUR
DO - 10.1070/MC2001v011n01ABEH001420
UR - https://mendcomm.colab.ws/publications/10.1070/MC2001v011n01ABEH001420
TI - Wedekind–Fock–Havinga salt Me(Et)N+(All)PhI–·CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration
T2 - Mendeleev Communications
AU - Kostyanovsky, Remir Grigorevich
AU - Kostyanovsky, Vasily Remirovich
AU - Kadorkina, Gulnara Konstantinovna
AU - Lyssenko, Konstantin Alexandrovich
PY - 2001
DA - 2001/02/22
PB - Mendeleev Communications
SP - 1-5
IS - 1
VL - 11
ER -
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@article{2001_Kostyanovsky,
author = {Remir Grigorevich Kostyanovsky and Vasily Remirovich Kostyanovsky and Gulnara Konstantinovna Kadorkina and Konstantin Alexandrovich Lyssenko},
title = {Wedekind–Fock–Havinga salt Me(Et)N+(All)PhI–·CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration},
journal = {Mendeleev Communications},
year = {2001},
volume = {11},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2001v011n01ABEH001420},
number = {1},
pages = {1--5},
doi = {10.1070/MC2001v011n01ABEH001420}
}
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Kostyanovsky, Remir Grigorevich, et al. “Wedekind–Fock–Havinga salt Me(Et)N+(All)PhI–·CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration.” Mendeleev Communications, vol. 11, no. 1, Feb. 2001, pp. 1-5. https://mendcomm.colab.ws/publications/10.1070/MC2001v011n01ABEH001420.
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Abstract

The title salt crystallises as a conglomerate (space group P212121, Z = 4) with one solvate CHCl3 molecule forming strong shortened contact with I– [Cl···I– 3.599(2) Å]. Therefore, it undergoes spontaneous resolution by simple crystallisation with a deficiency of the conglomerator CHCl3 or by an internal entrainment procedure. It exhibits the (S)-(+) absolute configuration and racemises in solution (ΔG#rac = 26.5 kcal mol–1). The salt was almost completely converted into one enantiomer by stirred crystallisation from solution (with full evaporation) or from a melt under conditions of enantiomerisation. The contribution of autocatalysis to this process is discussed.

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