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By Lewis G.N., Mayer J.E.

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28) Although the thermal IOOC reactions can sometimes be accomplished at 80 °C [64], the oxime olefins 242a–d and 245a, b required heating in toluene at 180 °C in a sealed tube. Thus tricyclic pyrrolidines 243a (anti) and 246a (anti), the indolizidines 243 b (anti:syn = 75:25), 243c (syn), and 246b (anti), and the quinolizidine 243d (syn) were isolated in 60–75% yield. It is noteworthy that the IOOC products 243a, 243c, 243d, 246a, and 246b were obtained stereochemically pure. Indolizidine 243b, on the other hand, was obtained as a mixture.

Kinetic and Thermodynamic Stability of 4-Lithio-1,3-dioxanes Experimental Studies . . . . . . . . . . . . Theoretical Studies . . . . . . . . . . . . . Synthetic Applications . . . . . . . . . . . . 5 Alternative Approaches to 1,3-Diol Synthesis . . . . . . 90 6 Conclusions . . . . . . . . . . . . . . . . 90 7 References . . . . . . . . . . . . . . . . 91 . . . . . 82 83 83 86 87 1 Introduction Polyol chains are common features in highly oxygenated natural products.

16) as is evident from the blue-green color which appears during the reaction. (16) The N-allylated compounds may serve as precursors to the N-unsubstituted pyrrolidines by a mild Pd(0) catalyzed deallylation procedure [45]. The deallylation may be more straightforward than hydrogenolysis of the N-benzylated product in which complications due to the presence of the oxime and the other Bn moiety (1,2 bond in the pyrrolidine ring) may arise during reduction. Attempts to prepare piperidine and azepine systems following the above procedure were unsuccessful.

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A Disproof of the Radiation Theory of Chemical Activation by Lewis G.N., Mayer J.E.


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