TY - JOUR
T1 - Preparation and chemistry of phi+c=ci+ph•2−otf, bis[phenyl[[(trifluoromethyl)sulfonyl]oxy]iodo]acetylene, a novel difunctional acetylene, bis(iodonium) species and a stable c2-transfer agent
AU - Stang, Peter J.
AU - Zhdankin, Viktor V.
PY - 1991/6/1
Y1 - 1991/6/1
N2 - The title compound 2 is readily prepared as a stable microcrystalline solid from bis(tri-n-butylstannyl)acetylene and PhlCN•OTf. It was fully characterized by multinuclear NMR, IR, and elemental analysis. As expected, the electron-deficient acetylene 2 reacts with a number of nucleophiles (e.g., Ph3P, PhSNa, and PhOLi) providing a variety of bifunctionalized acetylenes 5, 6, 7, and 9. It also undergoes cycloaddition reactions with cyclopentadiene, furan, and other 1,3-dienes to afford useful bis(iodonium)norbornadiene-type adducts 12–14.
AB - The title compound 2 is readily prepared as a stable microcrystalline solid from bis(tri-n-butylstannyl)acetylene and PhlCN•OTf. It was fully characterized by multinuclear NMR, IR, and elemental analysis. As expected, the electron-deficient acetylene 2 reacts with a number of nucleophiles (e.g., Ph3P, PhSNa, and PhOLi) providing a variety of bifunctionalized acetylenes 5, 6, 7, and 9. It also undergoes cycloaddition reactions with cyclopentadiene, furan, and other 1,3-dienes to afford useful bis(iodonium)norbornadiene-type adducts 12–14.
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U2 - 10.1021/ja00012a028
DO - 10.1021/ja00012a028
M3 - Article
AN - SCOPUS:0001744947
SN - 0002-7863
VL - 113
SP - 4571
EP - 4576
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 12
ER -