Work

Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors

Year: 2019

Type: article

Abstract: Silyl triflate precursors to cyclic alkynes and allenes serve as valuable synthetic building blocks. We report a concise and scalable synthetic approach to prepare the silyl triflate precursors to cyclohexyne and 1,2-cyclohexadiene. The strategy involves a retro-Brook rearrangement of an easily accessible cyclohexanone derivative, followed by triflation protocols. This simple, yet controlled, method should enable the further study of strained alkynes and allenes in chemical synthesis.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.8b03223

Authors: Jason V. Chari, Francesca M. Ippoliti, Neil K. Garg

Institution: University of California, Los Angeles

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: University of California, Los Angeles, National Institute of General Medical Sciences, National Center for Research Resources

Awards: Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical Research, Harnessing Strained Intermediates to Access Complex Molecules