In Memory of H.L. Meerwein by Boschke F.L. PDF

By Boschke F.L.

ISBN-10: 0387093095

ISBN-13: 9780387093093

ISBN-10: 3540093095

ISBN-13: 9783540093091

Content material: Brown, H. C. Meerwein and equilibrating carbocations. -- Olah, G. A. From boron trifluoride to antimony pentafluoride looking for strong carbocations. -- Hogeveen, H. and van Kruchten, E. M. G. A. Wagner-Meerwein rearrangements in long-lived polymethyl substituted bicyclo(3.2.0)heptadienyl cations. -- Kirmse, W. Rearrangements of carbocations

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Olah L3C NMR spectral investigations have been extended163b) to the study of he teroaromatic stabilized 6 ~r,3-dioxolium and 10 7r benzo-l,3-dioxolium ions 122 and 123. 122 123 Carboxylic acids are protonated in superacid media, such as F S O 3 H - S b F s SO2, H F - S b F s, or H F - B F 3 166) The NMR spectrum of acetic acid in such media at low temperature shows two OH resonances indicating (i) that carbonyl protonation is favored and (ii) that hindered rotation about the resultant COH bonds is present.

J I I I 1 I 9 8 7 6 5 Fig. 6. The 270-MHz FT IH-NMR spectrum of the "static" benzenium ion in SbF5-FSO3H-SO2CIF-SO2F 2 solution at -140 ~ I 46 I I I 10 9 8 I 1 7 6 ~ (ppm) 1 5 Fig. 7. 100-MHz 1H-NMRspectrum of the naphthalenium ion (31) at -90 ~ mona-, di-, tri-, tetra- and pentaalkylbenzenium and halobenzenium ions have been observed 88-89). Alkylation, nitration, halogenation etc. of hexamethyl benzene gives the related ions. Doering and Saunders prepared the very stable heptamethylbenzenium ion 87) 32.

CH3 ~--C~cH eclipsed a bisected 17 A wide range of studies 55' 60-627 have indicated that a cyclopropyl group is equal or more effective than a phenyl group in stabilizing an adjacent carbocation center. In contrast to "classical" tertiary and secondary cyclopropylmethyl cations (showing substantial charge delocalization into the cyclopropane ring but maintaining its identity) primary cyclopropylmethyl cations in contrast show compeltely a-delocalized non-classical carbonium ion character (see subsequent discussion).

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In Memory of H.L. Meerwein by Boschke F.L.

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