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

Weizmann Institute of Science, Ben-Gurion University of the Negev, Ariel University

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

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 Sep 2023
DOIs	https://doi.org/10.1021/acs.joc.3c00873
State	Published - 6 Oct 2023

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Thioxobimanes",

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.",

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T1 - Thioxobimanes

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

Y1 - 2023/10/6

N2 - 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.

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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U2 - 10.1021/acs.joc.3c00873

DO - 10.1021/acs.joc.3c00873

M3 - مقالة

C2 - 37712568

SN - 0022-3263

VL - 88

SP - 13475

EP - 13489

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Thioxobimanes

Abstract

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