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Insights into sulfinate formation from tosyl hydrazides
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Biochemistry.
2012 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 53, no 9, 1045-1047 p.Article in journal (Refereed) Published
Abstract [en]

Benzylation of 1,2-ditosylhydrazine in DMF under various basic conditions results in a benzyl sulfone via intermediary sulfinate formation, providing new insights and allowing practical conclusions to be drawn. The half-lives of 1,2-ditosylhydrazine and several monotosylated hydrazides with 1,1,3,3-tetramethylguanidine in DMSO have been determined by H-1 NMR spectroscopy and are found to vary from a few minutes to several months. In the course of this work a benzylated, partly detosylated compound has been identified and a 1,1,3,3-tetramethyl guanidine-containing side-product characterized. A contradictory report is also commented on.

Place, publisher, year, edition, pages
2012. Vol. 53, no 9, 1045-1047 p.
Keyword [en]
Half-life determination, Hydrazide cleavage, Nitrogen formation, Sulfinate, Sulfone
National Category
Chemical Sciences
URN: urn:nbn:se:uu:diva-172846DOI: 10.1016/j.tetlet.2011.12.061ISI: 000301833600010OAI: oai:DiVA.org:uu-172846DiVA: diva2:516155
Available from: 2012-04-17 Created: 2012-04-16 Last updated: 2012-04-17Bibliographically approved

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