TY - JOUR
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
N1 - Publisher Copyright:
© 2023 American Chemical Society.
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.
UR - https://www.scopus.com/pages/publications/85174289136
U2 - 10.1021/acs.joc.3c00873
DO - 10.1021/acs.joc.3c00873
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AN - SCOPUS:85174289136
SN - 0022-3263
VL - 88
SP - 13475
EP - 13489
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -