Reaction of Tin Porphyrins with Vicinal Diols
Date
Authors
Major Professor
Advisor
Committee Member
Journal Title
Journal ISSN
Volume Title
Publisher
Authors
Research Projects
Organizational Units
The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
History
The Department of Chemistry was founded in 1880.
Dates of Existence
1880-present
Related Units
- College of Liberal Arts and Sciences (parent college)
Journal Issue
Is Version Of
Versions
Series
Department
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.
Comments
Reprinted (adapted) with permission from Inorganic Chemistry 43 (2004): 2379, doi:10.1021/ic035123+. Copyright 2004 American Chemical Society.