Campus Units
Chemistry
Document Type
Article
Publication Version
Published Version
Publication Date
3-2004
Journal or Book Title
Inorganic Chemistry
Volume
43
Issue
7
First Page
2379
Last Page
2386
DOI
10.1021/ic035123+
Abstract
Reactions of tin porphyrins with vicinal diols were investigated. Treatment of (TTP)Sn(C⋮CPh)2or (TTP)Sn(NHtolyl)2 with pinacol and 2,3-diphenylbutane-2,3-diol afforded diolato complexes (TTP)Sn[OC(Me)2C(Me)2O] (1) and (TTP)Sn[OC(Ph)(Me)C(Ph)(Me)O] (2), respectively. Both complexes underwent C−C cleavage reactions to give (TTP)SnII and ketones. Reaction of (TTP)Sn(C⋮CPh)2 with 1 equivalent of o-catechol generated (TTP)Sn(C⋮CPh)(OC6H4OH) (3), which subsequently transformed into (TTP)Sn(OC6H4O) (4). With excess catechol, disubstituted (TTP)Sn(OC6H4OH)2 (5) was obtained. (TTP)Sn(C⋮CPh)(OCHRCHROH) (R = H, 6; R = Ph, 8) and (TTP)Sn(OCHRCHROH)2 (R = H, 7; R = Ph, 9) were obtained analogously by treatment of (TTP)Sn(C⋮CPh)2 with appropriate diols. In the presence of dioxygen, tin porphyrin complexes were found to promote the oxidative cleavage of vicinal diols and the oxidation of α-ketols to α-diketones. Possible reaction mechanisms involving diolato or enediolato intermediates are discussed. The molecular structure of (TTP)Sn(C⋮CPh)(OC6H4OH) (3) was determined by X-ray crystallography.
Copyright Owner
American Chemical Society
Copyright Date
2004
Language
en
File Format
application/pdf
Recommended Citation
Du, Guodong; Ellern, Arkady; and Woo, L. Keith, "Reaction of Tin Porphyrins with Vicinal Diols" (2004). Chemistry Publications. 783.
https://lib.dr.iastate.edu/chem_pubs/783
Comments
Reprinted (adapted) with permission from Inorganic Chemistry 43 (2004): 2379, doi:10.1021/ic035123+. Copyright 2004 American Chemical Society.