10129-51-8Relevant articles and documents
GEAR EFFECT-10 CONFORMATIONAL ASPECTS OF THE POSITIVE OR NEGATIVE BUTTRESSING EFFECTS OF METHYL GROUPS: POLYMETHYLPYRIDINES
Roussel, Christian,Balaban, Alexandru T.,Berg, Ulf,Chanon, Michel,Gallo, Roger,et al.
, p. 4209 - 4220 (1983)
The effects of the shape of a methyl group on reactivity, which cannot be accounted for by considering a methyl group as a spherical subtituent with the appropriate van der Waals radius, was considered in kinetics of alkylation of substituted pyridines and barriers to rotation and ground state conformations of an isopropyl group attached to a planar framework.The perturbation of a methyl group by an o-methyl group is accounted for by a unique conformational explanation which involves the polyhedral shape of the methyl group.
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Phillips
, p. 3296 (1952)
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Seeman, Jeffrey I.,Galzerano, Roseanne,Curtis, Keith,Schug, John C.,Viers, Jimmy W.
, p. 5982 - 5984 (1981)
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Competing processes in the photochemistry of picolines and their N-methyl salts: photoinduced charge transfer, phototransposition and photohydration
Bla?ek Bregovi?, Vesna,Basari?, Nikola
, p. 859 - 871 (2017/02/10)
Photochemical reactivity of a series of picolines and their N-methylated salts has been investigated by preparative irradiations and UV–vis spectroscopy. Understanding competing photochemical processes and knowledge of their relative efficiencies is important in the application of pyridines as photocages or in the synthesis of complex polycycles. Contrary to previous reports for the gas phase, picolines are not reactive in the phototransposition, presumably due to protonation of the pyridine nitrogen in the excited state. Deuterium exchange was observed upon irradiation in CD3CN–D2O, but it was rationalized by photoionization and radical formation. On the other hand, N-methylated picoline salts are not protonated upon excitation. They undergo photohydration and phototransposition (ΦR?=?0.01–0.06). Upon irradiation of iodides, azabicyclic [3.1.0] hydration products were obtained. A difference in product distribution was observed between iodides and perchlorates, due to photoelimination of perchloric acid leading to the thermal aziridine ring opening. Moreover, excitation of iodide derivatives gives rise to change transfer transition forming iodide radicals that eventually give I3 ? with the quantum efficiency ΦR?=?0.015–0.02.
[2+ + 4] Cycloadditions of iminium ions - Concerted or stepwise mechanism aza Diels - Alder reactions?
Mayr, Herbert,Ofial, Armin R.,Sauer, Juergen,Schmied, Bernhard
, p. 2013 - 2020 (2007/10/03)
The N,N-dimethylmethyleneammoninm ion 1 reacts regio- and stereoselectively with the 1,3-dienes 2a-2f to yield the 1,2',5,6- tetrahydropyridinium ions 3. The kinetics of these hetero Diels-Alder reactions, which have been followed by dilatometry and