Synthesis of Methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate via a Hofmann Rearrangement Utilizing Trichloroisocyanuric Acid as an Oxidant

A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, aryl, benzyl, and nitro groups.

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2011-01, Vol.76 (1), p.277-280
Hauptverfasser:	Crane, Zackary D, Nichols, Paul J, Sammakia, Tarek, Stengel, Peter J
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Magnetic Resonance Spectroscopy Organic chemistry Oxidants - chemistry Preparations and properties Stereoisomerism Vinyl Compounds - chemical synthesis Vinyl Compounds - chemistry
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Beschreibung
Zusammenfassung:	A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, aryl, benzyl, and nitro groups.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo101504e