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Chemical Structure| 92-85-3 Chemical Structure| 92-85-3
Chemical Structure| 92-85-3

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Product Citations

Min Ji Kim ; Diana J. Wang ; Karina Targos ; Uriel A. Garcia ; Alison F. Harris ; Ilia A. Guzei , et al.

Abstract: Cyclopropanes are desirable structural motifs with valuable applications in drug discovery and beyond. Established alkene cyclopropanation methods give rise to cyclopropanes with a limited array of substituents, are difficult to scale, or both. Herein, we disclose a new cyclopropane synthesis through the formal coupling of abundant carbon pronucleophiles and unactivated alkenes. This strategy exploits dicationic adducts derived from electrolysis of thianthrene in the presence of alkene substrates. We find that these dielectrophiles undergo cyclopropanation with methylene pronucleophiles via alkenyl thianthrenium intermediates. This protocol is scalable, proceeds with high diastereoselectivity, and tolerates diverse functional groups on both the alkene and pronucleophile coupling partners. To validate the utility of this new procedure, we prepared an array of substituted analogs of an established cyclopropane that is en route to multiple pharmaceuticals.

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Product Details of Thianthrene

CAS No. :92-85-3
Formula : C12H8S2
M.W : 216.32
SMILES Code : C12=CC=CC=C1SC3=C(C=CC=C3)S2
MDL No. :MFCD00005065
InChI Key :GVIJJXMXTUZIOD-UHFFFAOYSA-N
Pubchem ID :7109

Safety of Thianthrene

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
 

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