Issue 3, 2024

Grinding and the anisotropic environment: influences on the diastereoselective formation of Group 15 allyl complexes

Abstract

The heavy Group 15 allyls Image ID:d4mr00001c-t1.gif (E = As, Sb, Bi; [A′] = [1,3-(SiMe3)2C3H3]) can be prepared either in solution or mechanochemically, and exist in two diastereomeric forms of C1 and C3 symmetry. For E = As and Sb, their ratio varies with the method of preparation: the C1 diastereomer is the major form by both methods, but the mechanochemical route increases the C1 : C3 ratio compared to synthesis in hexanes solution. The difference in selectivity has previously been identified as a consequence of the layered crystal lattices of the EX3 reagents, which provide a templating effect through an anisotropic grinding environment. How this selectivity changes with other typical mechanochemical variables is explored here, including the use of different reagents and LAG solvents, pre-grinding the reagents, the use of different milling media (stainless steel, Teflon, etc.) and apparatus (mixer mill, planetary mill), and the number and size of balls. The extent to which the anisotropic environment is either maintained or modified during synthesis (especially by LAG and the choice of metal reagent) affects the diastereomeric ratio.

Graphical abstract: Grinding and the anisotropic environment: influences on the diastereoselective formation of Group 15 allyl complexes

Supplementary files

Article information

Article type
Paper
Submitted
04 Jan 2024
Accepted
21 Mar 2024
First published
27 Mar 2024
This article is Open Access
Creative Commons BY license

RSC Mechanochem., 2024,1, 235-243

Grinding and the anisotropic environment: influences on the diastereoselective formation of Group 15 allyl complexes

L. E. Wenger and T. P. Hanusa, RSC Mechanochem., 2024, 1, 235 DOI: 10.1039/D4MR00001C

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