Thioxobimanes

Partha Jyoti Das; Ankana Roy; Ashim Nandi; Ishita Neogi; Yael Diskin-Posner; Vered Marks; Iddo Pinkas; Sara Amer; Sebastian Kozuch; Michael Firer; Michael Montag; Flavio Grynszpan

doi:10.1021/acs.joc.3c00873

Thioxobimanes

Partha Jyoti Das, Ankana Roy, Ashim Nandi, Ishita Neogi, Yael Diskin-Posner, Vered Marks, Iddo Pinkas, Sara Amer, Sebastian Kozuch, Michael Firer, Michael Montag^*, Flavio Grynszpan

^*Corresponding author for this work

Department of Chemical Research Support

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

Dioxobimanes, colloquially known as bimanes, are a well-established family of N-heterobicyclic compounds that share a characteristic core structure, 1,5-diazabicyclo[3.3.0]octadienedione, bearing two endocyclic carbonyl groups. By sequentially thionating these carbonyls in the syn and anti isomers of the known (Me,Me)dioxobimane, we were able to synthesize a series of thioxobimanes, representing the first heavy-chalcogenide bimane variants. These new compounds were extensively characterized spectroscopically and crystallographically, and their aromaticity was probed computationally. Their potential role as ligands for transition metals was demonstrated by synthesizing a representative gold(I)-thioxobimane complex.

Original language	English
Pages (from-to)	13475-13489
Number of pages	15
Journal	Journal of Organic Chemistry
Volume	88
Issue number	19
Early online date	15 Sept 2023
DOIs	https://doi.org/10.1021/acs.joc.3c00873
Publication status	Published - 6 Oct 2023

Funding

This work was funded by the Research and Development Authority, Ariel University (grants RA1500000015, RA1600000415). F.G. is the incumbent of the Cosman endowment for organic chemistry research. I.P. is the incumbent of the Sharon Zuckerman Research Fellow chair. We thank Dr. Itay Pitussi (Ariel University) for conducting HRMS measurements.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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Cite this

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AU - Das, Partha Jyoti

AU - Roy, Ankana

AU - Nandi, Ashim

AU - Neogi, Ishita

AU - Diskin-Posner, Yael

AU - Marks, Vered

AU - Pinkas, Iddo

AU - Amer, Sara

AU - Kozuch, Sebastian

AU - Firer, Michael

AU - Montag, Michael

AU - Grynszpan, Flavio

PY - 2023/10/6

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AB - Dioxobimanes, colloquially known as bimanes, are a well-established family of N-heterobicyclic compounds that share a characteristic core structure, 1,5-diazabicyclo[3.3.0]octadienedione, bearing two endocyclic carbonyl groups. By sequentially thionating these carbonyls in the syn and anti isomers of the known (Me,Me)dioxobimane, we were able to synthesize a series of thioxobimanes, representing the first heavy-chalcogenide bimane variants. These new compounds were extensively characterized spectroscopically and crystallographically, and their aromaticity was probed computationally. Their potential role as ligands for transition metals was demonstrated by synthesizing a representative gold(I)-thioxobimane complex.

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Thioxobimanes

Abstract

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