TY - JOUR
T1 - Can the absence of solvation of neutral reagents by ionic liquids be responsible for the high reactivity in base-assisted intramolecular nucleophilic substitutions in these solvent?
AU - Frenna, Vincenzo
AU - Noto, Renato
AU - D'Anna, Francesca
AU - Spinelli, Domenico
AU - Pace, Vitalba
PY - 2005
Y1 - 2005
N2 - The kinetics of the rearrangement of the Z-phenylhydrazoneof 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1a) into the relevant4-benzoylamino-2,5-diphenyl-1,2,3-triazole (2a) induced byamines have been studied in two room-temperature ionicliquids (IL-1, [BMIM][BF4] and IL-2, [BMIM][PF6]). Thedata collected show that the reaction occurs faster in ionicliquids than in other conventional solvents previouslystudied (both polar or apolar, protic or aprotic). Presumably,this could depend on their peculiar ability to minimize thestrong substrate-solvent, amine-solvent and amine-amineinteractions occurring in conventional solvents.
AB - The kinetics of the rearrangement of the Z-phenylhydrazoneof 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1a) into the relevant4-benzoylamino-2,5-diphenyl-1,2,3-triazole (2a) induced byamines have been studied in two room-temperature ionicliquids (IL-1, [BMIM][BF4] and IL-2, [BMIM][PF6]). Thedata collected show that the reaction occurs faster in ionicliquids than in other conventional solvents previouslystudied (both polar or apolar, protic or aprotic). Presumably,this could depend on their peculiar ability to minimize thestrong substrate-solvent, amine-solvent and amine-amineinteractions occurring in conventional solvents.
UR - http://hdl.handle.net/10447/34440
M3 - Book/Film/Article review
SN - 0022-3263
VL - 70
SP - 2828
EP - 2831
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
ER -