A clean and efficient synthesis of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles using silver tetrafluoroborate as a fluorodesulfurization reagent

Karl Hemming, Dexter T. Morgan, Robert K. Smalley

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

5-Ethylthio-6,6,7,7-tetramethyl substituted 4-oxa-1,3-diazabicyclo[3.2.0]hept-2-enes undergo fluorodesulfurization with silver tetrafluoroborate to furnish high yields of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles. Ethylthio substituted 1,2,4-triaza- and 1,3-diaza-bicyclo[3.2.0]hept-2-enes behave in a similar fashion to yield 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-triazoles and imidazoles, respectively.

Original languageEnglish
Pages (from-to)83-86
Number of pages4
JournalJournal of Fluorine Chemistry
Volume106
Issue number1
DOIs
Publication statusPublished - 1 Oct 2000
Externally publishedYes

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Imidazoles
Oxadiazoles
imidazoles
reagents
silver
synthesis
silver tetrafluoroborate
1,2,4-triazole

Cite this

@article{f4ec699902b4404eb20ec62972a53235,
title = "A clean and efficient synthesis of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles using silver tetrafluoroborate as a fluorodesulfurization reagent",
abstract = "5-Ethylthio-6,6,7,7-tetramethyl substituted 4-oxa-1,3-diazabicyclo[3.2.0]hept-2-enes undergo fluorodesulfurization with silver tetrafluoroborate to furnish high yields of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles. Ethylthio substituted 1,2,4-triaza- and 1,3-diaza-bicyclo[3.2.0]hept-2-enes behave in a similar fashion to yield 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-triazoles and imidazoles, respectively.",
keywords = "1,2,4-Oxadiazoles, 1,2,4-Triazoles, Fluoroalkyl substituted heterocycles, Fluorodesulfurization, Silver tetrafluoroborate",
author = "Karl Hemming and Morgan, {Dexter T.} and Smalley, {Robert K.}",
year = "2000",
month = "10",
day = "1",
doi = "10.1016/S0022-1139(00)00313-4",
language = "English",
volume = "106",
pages = "83--86",
journal = "Journal of Fluorine Chemistry",
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publisher = "Elsevier BV",
number = "1",

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TY - JOUR

T1 - A clean and efficient synthesis of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles using silver tetrafluoroborate as a fluorodesulfurization reagent

AU - Hemming, Karl

AU - Morgan, Dexter T.

AU - Smalley, Robert K.

PY - 2000/10/1

Y1 - 2000/10/1

N2 - 5-Ethylthio-6,6,7,7-tetramethyl substituted 4-oxa-1,3-diazabicyclo[3.2.0]hept-2-enes undergo fluorodesulfurization with silver tetrafluoroborate to furnish high yields of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles. Ethylthio substituted 1,2,4-triaza- and 1,3-diaza-bicyclo[3.2.0]hept-2-enes behave in a similar fashion to yield 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-triazoles and imidazoles, respectively.

AB - 5-Ethylthio-6,6,7,7-tetramethyl substituted 4-oxa-1,3-diazabicyclo[3.2.0]hept-2-enes undergo fluorodesulfurization with silver tetrafluoroborate to furnish high yields of 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-oxadiazoles. Ethylthio substituted 1,2,4-triaza- and 1,3-diaza-bicyclo[3.2.0]hept-2-enes behave in a similar fashion to yield 5-(2′-fluoro-2′,3′-dimethylbutan-3′-yl) substituted 1,2,4-triazoles and imidazoles, respectively.

KW - 1,2,4-Oxadiazoles

KW - 1,2,4-Triazoles

KW - Fluoroalkyl substituted heterocycles

KW - Fluorodesulfurization

KW - Silver tetrafluoroborate

UR - http://www.scopus.com/inward/record.url?scp=0003735632&partnerID=8YFLogxK

U2 - 10.1016/S0022-1139(00)00313-4

DO - 10.1016/S0022-1139(00)00313-4

M3 - Article

VL - 106

SP - 83

EP - 86

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

IS - 1

ER -