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Synfacts 2024; 20(06): 0581
DOI: 10.1055/s-0043-1763944
Synthesis of Materials and Unnatural Products

Regioselectivity in Mechanochemistry

Contributor(s):
Dahui Zhao
,
Lihui Guo
Ding S, Wang W, Germann A, Wei Y, Du T, Meisner J, *, Zhu R, *, Liu Y. * Heinrich Heine Universität Düsseldorf, Germany and Peking University, Beijing, P. R. of China
Bicyclo[2.2.0]hexene: A Multicyclic Mechanophore with Reactivity Diversified by External Forces.

J. Am. Chem. Soc. 2024;
146: 6104-6113
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Key words

mechanochemistry - mechanophore - bicyclo[2.2.0]hexene - regioselectivity

Significance

The reaction selectivity of mechanophores is supposedly dependent on the direction of applied mechanical force, the experimental proof of which is demonstrated herein. A set of bicyclo[2.2.0]hexene (BCH) mechanophores having polymer substituents tethered at different positions are synthesized and shown to go down predictable reaction paths upon sonication.


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Comment

The ring-opening metathesis polymerizations of cis-cyclooctene are first conducted with various BCH derivatives introduced as the comonomer. In spite of the different substitution positions of the BCH mechanophores, predicted bond scission consistently occurs between the polymer-­anchoring carbons.


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Publication History

Article published online:
14 May 2024

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