Detail of "4453-90-1"

Reference

Kinetics and mechanism of addition of acids to olefins

Kinetics and mechanism of addition of acids to olefins. Part I. Addition of acetic acid to cyclic and strained bicyclic olefins catalyzed by trifluoromethanesulfonic acid. Roberts, Roger M. G. (Dep. Chem., Univ. Essex, Colchester, Engl.). J. Chem. Soc., Perkin Trans. 2, (10), 1183-90 (English) 1976. CODEN: JCPKBH. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) The F3CSO3H-catalyzed addn. of AcOH to cyclic and strained bicyclic olefins was investigated. 4453-90-1 and 5989-27-5 are cas registry numbers of chemicals which are used as reagents here. Addn. to norbornene and related compds. was 1st order with respect to F3CSO3H but for cyclohexene a small contribution from a 2nd order term was obsd. The addn. was nonstereospecific. Kinetic isotope effects were <1 for cyclic substrates and >1 for norbornene indicating a change to rate-detg. proton transfer. Activation parameters for the reaction and H0 for F3CSO3H in AcOH are reported. The addn. is discussed in terms of intimate and solvent-sepd. ion pairs. .

Evidence for the intermediacy of discrete classical carbanions in the rearrangements of the 5-norbornenyl and benzonorbornenyl systems

Evidence for the intermediacy of discrete classical carbanions in the rearrangements of the 5-norbornenyl and benzonorbornenyl systems. Paddon-Row, Michael N.; Butler, Douglas N.; Warrener, Ronald N. (Dep. Chem., New South Wales Inst. 38931-86-1 and 4453-90-1 are also occured in this study. Technol., Broadway, Aust.). J. Chem. Soc., Chem. Commun., (18), 741-2 (English) 1976. CODEN: JCCCAT. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) The carbanions in the title series were generated by Birch redn. of norbornadiene and benzonorbornadiene. The redn. of norbornadiene (Na, NH3(l), -33.degree., THF as cosolvent, Me3COH as proton source) gave a 1:19 mixt. of nortricyclene and norbornene. 1H D labeling studies suggest the exclusive presence of the classical species (I) and (II) whose rate of interconversion is slow at -33.degree. and rapid at 60.degree.. In the case of benzonorbornadiene redn., D labeling confirms the intermediacy of two slowly interconverting classical ions III (R = H, R1 = D; R = D, R1 = H). .