By S.L. Schreiber
Quantity 1 presents an in depth survey of reactions that entail the 1,2-addition of nonstabilized carbanion equivalents of carbonyl, imino and thiocarbonyl performance. Emphasis has been put on these reagents that bring about hugely selective addition reactions. tools are suggested to pick, for instance, one carbonyl team over one other within the comparable molecule, or so as to add preferentially a fraction to at least one (enantiotopic of diastereotopic) face of a carbonyl team. methods that outcome from an preliminary addition to the C=X useful staff, for instance alkenations and rearrangements, also are coated during this quantity.
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Extra info for Additions to C-X &pgr;-Bonds, Part 1, Volume 1
The separation of the two basic sites in 71 (and 74) by the alkane chain increases the chelation effect against the proton. The size of IMHB effect depends on the strength of the basic sites that can chelate the proton and the geometry of monocations, which favours the formation of the IMHB. Direct azinyl substitution on the imino nitrogen in formamidines, leads to proton chelation and IMHB, similar to 74. However, gas phase basicity values are below the superbasicity threshold, due to less effective cation stabilization by n-p conjugation of the amidine with aza groups .
However, P2 and P3 iminophosphoranes and phosphoranes, which contain several phosphorus atoms, are stronger bases than 138, 149 or 148. Although theory indicated that 146 would be more basic than 139, experiments by Verkade in acetonitrile showed the opposite . This was rationalized by the more distant polarizing proton from the lone pair on axial nitrogen in 143Hþ than in 139Hþ which is fully transannulated. Solvation effects probably play a significant role. The same authors confirmed experimentally that 145 is more basic than 139.
7). 8). 2] tetraamine 57 (cross-bridged cyclam) is capable of adopting conformations having all four nitrogen lone pairs pointing towards the cavity centre. 32 in acetonitrile) . Cage-adamanzanes such as 6adamanzane 58 capture a proton, which in solution rapidly shuttles between all four nitrogen atoms. All the nitrogen lone pairs in the polyaza cage were pointed inward toward the cation, so the complex enjoys both thermodynamic and kinetic stability . 7 Structures of polycyclic polyamines 53–56 even alkali metal solutions in ammonia and amines, so the pKa values for protonated cages remains unknown .
Additions to C-X &pgr;-Bonds, Part 1, Volume 1 by S.L. Schreiber