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Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.

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.

SUBMITTER: Chari JV

PROVIDER: S-EPMC6935045 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.

Chari Jason V JV Ippoliti Francesca M FM Garg Neil K NK

The Journal of organic chemistry 20190306 6

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. ...[more]

PMID: 30840455

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