Preparation of Trifluoromethyl Lactol Derivatives via Base Initiated Cyclobutanol Ring Opening to a Laterally Lithiated Trifluoromethyl Ketone

Daniel Becker; Daniel L. Flynn

doi:10.1055/s-1996-5325

Preparation of Trifluoromethyl Lactol Derivatives via Base Initiated Cyclobutanol Ring Opening to a Laterally Lithiated Trifluoromethyl Ketone

Daniel Becker, Daniel L. Flynn

Department of Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Benzocyclobutenone derivatives 4 are converted to the corresponding trifluoromethylcyclobutanols 5 by treatment with trifluoromethyltrimethylsilane in the presence of tetra-n-butylammonium fluoride. These trifluoromethylcyclobutanol derivatives are then treated with LiTMP in the presence of aromatic aldehydes to afford trifluoromethyllactols 6 via a laterally-lithiated trifluoromethylketone intermediate.

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	1996
Issue number	1
DOIs	https://doi.org/10.1055/s-1996-5325
State	Published - Jan 1 1996

Keywords

ketones
trifluoromethyl lactol derivates

Disciplines

Chemistry

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Preparation of Trifluoromethyl Lactol Derivatives via Base InitiFinal published version, 123 KBLicense: Unspecified

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title = "Preparation of Trifluoromethyl Lactol Derivatives via Base Initiated Cyclobutanol Ring Opening to a Laterally Lithiated Trifluoromethyl Ketone",

abstract = " Benzocyclobutenone derivatives 4 are converted to the corresponding trifluoromethylcyclobutanols 5 by treatment with trifluoromethyltrimethylsilane in the presence of tetra-n-butylammonium fluoride. These trifluoromethylcyclobutanol derivatives are then treated with LiTMP in the presence of aromatic aldehydes to afford trifluoromethyllactols 6 via a laterally-lithiated trifluoromethylketone intermediate.",

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author = "Daniel Becker and Flynn, {Daniel L.}",

year = "1996",

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doi = "10.1055/s-1996-5325",

language = "American English",

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journal = "Chemistry: Faculty Publications and Other Works",

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AU - Flynn, Daniel L.

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Y1 - 1996/1/1

N2 - Benzocyclobutenone derivatives 4 are converted to the corresponding trifluoromethylcyclobutanols 5 by treatment with trifluoromethyltrimethylsilane in the presence of tetra-n-butylammonium fluoride. These trifluoromethylcyclobutanol derivatives are then treated with LiTMP in the presence of aromatic aldehydes to afford trifluoromethyllactols 6 via a laterally-lithiated trifluoromethylketone intermediate.

AB - Benzocyclobutenone derivatives 4 are converted to the corresponding trifluoromethylcyclobutanols 5 by treatment with trifluoromethyltrimethylsilane in the presence of tetra-n-butylammonium fluoride. These trifluoromethylcyclobutanol derivatives are then treated with LiTMP in the presence of aromatic aldehydes to afford trifluoromethyllactols 6 via a laterally-lithiated trifluoromethylketone intermediate.

KW - ketones

KW - trifluoromethyl lactol derivates

UR - https://ecommons.luc.edu/chemistry_facpubs/12

U2 - 10.1055/s-1996-5325

DO - 10.1055/s-1996-5325

M3 - Article

VL - 1996

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 1

ER -

Preparation of Trifluoromethyl Lactol Derivatives via Base Initiated Cyclobutanol Ring Opening to a Laterally Lithiated Trifluoromethyl Ketone

Abstract

Keywords

Disciplines

Access to Document

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