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An unprecedented rearrangement of a 1,1-diprotected hydrazine derivative. Structure revision of a catalyst-containing by-product
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Biochemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC. (avliden)
2014 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 55, no 51, 7019-7022 p.Article in journal (Refereed) Published
Abstract [en]

Treatment of 1-Boc-1-tosyl-hydrazine with 1,1,3,3-tetramethylguanidine (TMG) gave rise to twoproducts, one containing and the other not containing TMG. The latter was identified as 1-Boc-2-tosylhydrazine.This rearrangement provided useful insight into the nature of the first product that had previouslybeen isolated and assigned an incorrect tentative structure. To rationalize the results a plausiblemechanism via a common intermediate, involving TMG as a nucleophilic catalyst is proposed. A simplerprocedure for the preparation of the starting material is also presented.

Place, publisher, year, edition, pages
Elsevier, 2014. Vol. 55, no 51, 7019-7022 p.
Keyword [en]
Hydrazine derivative; Nucleophilic catalysis; Rearrangement; Structure revision; Tetramethylguanidine
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-239448DOI: 10.1016/j.tetlet.2014.10.121ISI: 000347020100015OAI: oai:DiVA.org:uu-239448DiVA: diva2:774585
Available from: 2014-12-26 Created: 2014-12-26 Last updated: 2017-12-05Bibliographically approved

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Ragnarsson, Ulf

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