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

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posted on 2024-11-15, 00:08 authored by James K Howard, Chintan Amin, Brendan Lainhart, Jason A Smith, Jack Rimington, Christopher HylandChristopher Hyland
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.

History

Citation

Howard, J. K., Amin, C., Lainhart, B., Smith, J. A., Rimington, J. & Hyland, C. J. T. (2014). Synthesis of nitrogen-substituted methylenecyclopropanes by strain-driven overman rearrangement of cyclopropenylmethyl trichloroacetimidates. Journal of Organic Chemistry, 79 (17), 8462-8468.

Journal title

Journal of Organic Chemistry

Volume

79

Issue

17

Pagination

8462-8468

Language

English

RIS ID

94384

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