By Boschke F.L.
Content material: thought of orientation and stereoselection / ok. Fukui -- fresh advancements within the chemistry of the reduce boron hydrides / H.D. Johnson, S.G. Shore -- Preparative features of boron-nitrogen ring compounds / A. Meller -- 1,3,2-diazaboracycloalkanes / ok. Niedenzu, C.D. Miller -- Darstellung und Systematisierung von Boraten und Polyboraten / G. Heller -- Allene-Olefin and Allene-Allene cycloadditions ; Methylenecyclobutane and 1,2-dimethylenecyclobutane degenerate rearrangements / J.E. Baldwin, R.H. Fleming -- Nitrogen inversion, scan and thought / J.M. Lehn -- Konformative Beweglichkeit von Siebenring-Systemen -- creation to all-valence electrons S.C.F. ; Calculations of huge natural molecules: conception and purposes
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Additional info for Dynamic Stereochemistry
Azo compounds, diimides etc. g. rotation about the (X,Y,Z)-N single bonds or the X = N double bond. This situation holds, for instance, in acyclic amines (methylamine, h y d r o x y l a m i n e . . ) and in imines. Furthermore, nitrogen inversion may in some cases occur in the same molecule together with ring inversion, for instance, in piperidine. It will thus sometimes be necessary to distinguish between internal 313 J. M. Lehn rotation or ring inversion a n d nitrogen inversion. T h e w a y s of s e p a r a t i n g these processes will be discussed below.
S t r u c t u r a l E ff ects on N i t r o g e n I n v e r s i o n B a r r i e r s . . . . . . . . . . . 1. Steric Effects . . . . . . . . . . . . . . . . . . . . . . . . . . A. N o n - B o n d e d I n t e r a c t i o n s . . . . . . . . . . . . . . . . . . . . B. R i n g S t r a i n . . . . . . . . . . . . . . . . . . . . . . . . . . 2, E l e c t r o n i c Effects . . . . . . . . . . . . . . . . . .
The conjugative ability of the --OCH3 and -N(CH3)~ groups decreases the conjugation between the aziridine nitrogen and the carbonyl group, thus increasing the barrier to nitrogen inversion; the effect is larger for -N(CH3)2 which is a better conjugative group than -OCH~. In the homogeneous series of aziridines 36--41 where the nitrogen site bears an --C6H4--Y group, one observes a decrease in inversion barrier which parallels the ability of the substituent Y to withdraw electron density from the aromatic ring.