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

…, PJ Nichols, T Sammakia, PJ Stengel

Index: Crane, Zackary D.; Nichols, Paul J.; Sammakia, Tarek; Stengel, Peter J. Journal of Organic Chemistry, 2011 , vol. 76, # 1 p. 277 - 280

Full Text: HTML

Citation Number: 21

Abstract

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.

~66%

Atom??economy Synthesis of N??Substituted Carbamate from Ure...

[Guo, Xiaoguanga; Shang, Jianpenga; Li, Jiana; Wang, Liguoa; Ma, Yuboa; Shi, Feng; Deng, Youquan Chinese Journal of Chemistry, 2010 , vol. 28, # 2 p. 164 - 170]

Carbamoyl complexes as a source of isocyanates or carbamyl c...

[Giannoccaro, Potenzo; Tommasi, Immacolata; Aresta, Michele Journal of Organometallic Chemistry, 1994 , vol. 476, # 1 p. 13 - 18]

Synthesis of 5-membered cyclic carbonates by oxidative carbo...

[Giannoccaro, Potenzo Journal of Organometallic Chemistry, 1994 , vol. 470, # 1.2 p. 249 - 252]

The syntheses of carbamates from reactions of primary and se...

[Sima, Tianlong; Guo, Shu; Shi, Feng; Deng, Youquan Tetrahedron Letters, 2002 , vol. 43, # 45 p. 8145 - 8147]

Conversion of carbonimidodithioates to carbamates

[Anbazhagan, Mariappan; Reddy, T. Indrasena; Rajappa, Srinivasachari Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 11 p. 1623 - 1627]