TY - JOUR
T1 - 1-(organosulfonyloxy)-3(1H)-1,2-benziodoxoles
T2 - Preparation and reactions with alkynyltrimethylsilanes
AU - Zhdankin, Viktor
AU - Kuehl, Chris J.
AU - Krasutsky, Alexei P.
AU - Bolz, Jason T.
AU - Simonsen, Angela J.
PY - 1996/9/20
Y1 - 1996/9/20
N2 - Organosulfonyloxy derivatives of 1,2-benziodoxol-3(1H)-one (3a-c) and 3,3-bis(trifluoromethyl)-3(1H)-1,2-benziodoxole (5a-c) can be prepared in high yield by the reaction of 1-hydroxybenziodoxoles 1 or 4 and the corresponding sulfonic acids or Me3SiOTf in the form of stable, but moderately hygroscopic, microcrystalline solids. Reaction of the triflate derivatives 3a and 5a with alkynyltrimethylsilanes affords either alkynyliodonium triflates 6, or (E)-β-(trifluoromethanesulfonyloxy)-alkenyliodonium triflates 7, while the same reaction in the presence of pyridine selectively gives the respective 1-alkynylbenziodoxoles 8 and 9 in 82-90% yield.
AB - Organosulfonyloxy derivatives of 1,2-benziodoxol-3(1H)-one (3a-c) and 3,3-bis(trifluoromethyl)-3(1H)-1,2-benziodoxole (5a-c) can be prepared in high yield by the reaction of 1-hydroxybenziodoxoles 1 or 4 and the corresponding sulfonic acids or Me3SiOTf in the form of stable, but moderately hygroscopic, microcrystalline solids. Reaction of the triflate derivatives 3a and 5a with alkynyltrimethylsilanes affords either alkynyliodonium triflates 6, or (E)-β-(trifluoromethanesulfonyloxy)-alkenyliodonium triflates 7, while the same reaction in the presence of pyridine selectively gives the respective 1-alkynylbenziodoxoles 8 and 9 in 82-90% yield.
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U2 - 10.1021/jo960927a
DO - 10.1021/jo960927a
M3 - Article
AN - SCOPUS:0000111031
SN - 0022-3263
VL - 61
SP - 6547
EP - 6551
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -