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Issue 40, 2020
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Reversible switching between housane and cyclopentanediyl isomers: an isonitrile-catalysed thermal reverse reaction

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Abstract

The photo-isomerization of an isolable five-membered singlet biradical based on C, N, and P ([TerNP]2CNDmp, 2a) selectively afforded a closed-shell housane-type isomer (3a) by forming a transannular P–P bond. In the dark, the housane-type species re-isomerized to the biradical, resulting in a fully reversible overall process. In the present study, the influence of tBuNC on the thermal reverse reaction was investigated: the isonitrile acted as a catalyst, thus allowing control over the thermal reaction rate. Moreover, tBuNC also reacted with the biradical to form an adduct species ([TerNP]2CNDmp·CNtBu, 4a), which can be regarded as the resting state of the system. The reactive species 2a and 3a could be re-generated in situ by irradiation with red light. The results of this study extend our understanding of this new class of molecular switches.

Graphical abstract: Reversible switching between housane and cyclopentanediyl isomers: an isonitrile-catalysed thermal reverse reaction

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Supplementary files

Article information


Submitted
31 Jul 2020
Accepted
24 Aug 2020
First published
25 Aug 2020

Dalton Trans., 2020,49, 13986-13992
Article type
Paper

Reversible switching between housane and cyclopentanediyl isomers: an isonitrile-catalysed thermal reverse reaction

H. Beer, J. Bresien, D. Michalik, A. Schulz and A. Villinger, Dalton Trans., 2020, 49, 13986
DOI: 10.1039/D0DT02688C

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