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
AN - SCOPUS:0003735632
VL - 106
SP - 83
EP - 86
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
SN - 0022-1139
IS - 1
ER -