4-Nitrophenyltriflate and 4-Nitrophenylnonaflate as New Perfluoroalkanesulfonyl Transfer Agents: Experimental and Computational Studies

4-Nitrophenyl triflate (1) as well as 4-nitrophenyl nonaflate (2) are excellent perfluoroalkanesulfonyl transfer agents. An important feature of the present method is its chemoselectivity. The aliph. hydroxy function was inert under the reaction conditions studied , and consequently phenols can be selectively triflated in the presence of alc. Frontier MO calcns. were used to rationalize the exptl. results. [on SciFinder (R)]


Published in:
Journal of Organic Chemistry, 64, 20, 7638-7642
Year:
1999
Keywords:
Note:
CAN 131:299175
22-4
Physical Organic Chemistry
Institut de Chimie des Substances Naturelles,CNRS,Gif-Sur-Yvette,Fr.
Journal
0022-3263
written in English.
17763-80-3 (4-Nitrophenyl triflate); 32578-27-1 (2,4-Dinitrophenyl triflate); 32848-23-0 (4-Nitrophenyl nonaflate); 132993-22-7 (2-Nitrophenyl triflate) Role: PEP (Physical, engineering or chemical process), RCT (Reactant), PROC (Process), RACT (Reactant or reagent) (4-nitrophenyltriflate and 4-nitrophenylnonaflate as new perfluoroalkanesulfonyl transfer agents); 98-54-4; 135-19-3 (2-Naphthalenol); 540-38-5; 621-59-0; 3279-76-3; 20649-40-5; 247018-45-7; 247018-46-8 Role: RCT (Reactant), RACT (Reactant or reagent) (4-nitrophenyltriflate and 4-nitrophenylnonaflate as new perfluoroalkanesulfonyl transfer agents); 3857-83-8P; 7462-11-5P; 34859-82-0P; 42096-34-4P; 93131-74-9P; 109586-39-2P; 154318-75-9P; 154447-04-8P; 157790-73-3P; 199465-44-6P; 247018-48-0P; 247018-49-1P; 247018-50-4P; 247018-51-5P; 247018-52-6P Role: SPN (Synthetic preparation), PREP (Preparation) (4-nitrophenyltriflate and 4-nitrophenylnonaflate as new perfluoroalkanesulfonyl transfer agents)
Laboratories:




 Record created 2010-11-25, last modified 2018-01-28


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