Reaction of. mu.-oxobis [(trifluoromethanesulfonato)(phenyl) iodine (III)] with group 14 propargyl derivatives and a propargyl ether

…, JR Norton, MM Miller, OP Anderson

Index: Gately, Daniel A.; Luther, Thomas A.; Norton, Jack R.; Miller, Mary M.; Anderson, Oren P. Journal of Organic Chemistry, 1992 , vol. 57, # 24 p. 6496 - 6502

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Citation Number: 28

Abstract

The treatment of 4, 4dimethyl-l-(trimethylsilyl)-2-pntyne (4a) or 4, 4dimethyl-l-(tributylstannyl)- 2-pntyne (ab) with p-oxobie [(trifluoromethanesulfoaato) henyl) iodine (m)](2) gim 4, 4dimethyl-l-(% iodophenyl)-2-pentyne (9). Deuterium labeling has confiied that propargylation of 2 occurs ortho to the position originally occupied by the I (II1). The addition of 2 equiv of 4a to 2 at-80" C results in 2 equiv each of 9, trimethylsilyl triflate (lo), and tert- ...