Organic Chemistry

Heterocyclic Hypervalent Iodine(III) Compounds with Fused Benziodazole and Tetrazole Rings (I-Substituted Tetrazolo[1,5-b][1,2]Benziodazoles)

Authors

Abstract

A series of heterocyclic hypervalent (HV) iodine(III) compounds containing fused tetrazole and benziodazole rings, i.e., derivatives of benziodazolotetrazole (BIAT) with various ligands (L) attached to the iodine atom (BIAT-L) were prepared and studied. They were characterized by 1H and 13C NMR spectroscopy, ESI-HRMS, and X-ray crystallography. The thermal stabilities of all BIAT derivatives (L= Cl, OH, OAc, OMe) were studied and the degradation patterns as well as the enthalpies of degradation were measured by thermal gravimetric analysis coupled with differential scanning calorimetry. The reaction of various alkenes with BIAT-Cl in the presence of Cu(OTf)2 at room temperature yielded chloro-tetrazolylated products. The oxidation of thioanisole with BIAT-Cl under various reaction conditions is also reported.

Content

Thumbnail image of Heterocyclic HVI(III) Compounds with Fused Benziodazole and Tetrazole Rings - draft 5.pdf

Supplementary material

Thumbnail image of Heterocyclic HVI(III) Compounds with Fused Benziodazole and Tetrazole Rings - SI draft 5.pdf
Heterocyclic HVI(III) Compounds with Fused Benziodazole and Tetrazole Rings - SI draft 5
Thumbnail image of Heterocyclic HVI(III) Compounds with Fused Benziodazole and Tetrazole Rings - draft 5.docx
Heterocyclic HVI(III) Compounds with Fused Benziodazole and Tetrazole Rings - draft 5
Thumbnail image of Heterocyclic HVI(III) Compounds with Fused Benziodazole and Tetrazole Rings - SI draft 5.docx
Heterocyclic HVI(III) Compounds with Fused Benziodazole and Tetrazole Rings - SI draft 5
Thumbnail image of BIAT-Cl (3 mg) themal decomposition.mov
BIAT-Cl (3 mg) themal decomposition
Thumbnail image of BIAT-Cl (3 mg) rxn with Bu3P and DMSO.mov
BIAT-Cl (3 mg) rxn with Bu3P and DMSO