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Synthesis of nitrogen-substituted methylenecyclopropanes by strain-driven overman rearrangement of cyclopropenylmethyl trichloroacetimidates

Citation

Howard, JK and Amin, C and Lainhart, B and Smith, JA and Rimington, J and Hyland, CJT, Synthesis of nitrogen-substituted methylenecyclopropanes by strain-driven overman rearrangement of cyclopropenylmethyl trichloroacetimidates, The Journal of Organic Chemistry, 79, (17) pp. 8462-8468. ISSN 0022-3263 (2014) [Refereed Article]

Copyright Statement

Copyright 2014 American Chemical Society

DOI: doi:10.1021/jo501423u

Abstract

Nitrogen-substituted methylenecyclopropanes have been prepared by a strain-driven Overman rearrangement of cyclopropenylmethyl trichloroacetimidates. The reaction proceeds at room temperature and without the need of a transition-metal catalyst. Furthermore, it has been shown that C-3-substituted cyclopropenylmethyl trichloroacetimidates undergo a hydrolytic ring-opening reaction to form allenylcarbinols.

Item Details

Item Type:Refereed Article
Keywords:cyclopropenes, cyclopropanes
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Howard, JK (Mr James Howard)
Author:Smith, JA (Associate Professor Jason Smith)
ID Code:98954
Year Published:2014
Web of Science® Times Cited:10
Deposited By:Chemistry
Deposited On:2015-03-10
Last Modified:2017-10-25
Downloads:0

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