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π-Coordination of Diorganotin Dications

✍ Scribed by Prof. Dr. Bernd Wrackmeyer; Dipl.-Chem. Gerald Kehr; Dr. Roland Boese

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
367 KB
Volume
30
Category
Article
ISSN
0044-8249

No coin nor oath required. For personal study only.

✦ Synopsis

from the axial C-Oo bond to the LUMO of the system offsets to some degree the steric advantages enjoyed by its equatorial C-0 counterpart.

Whatever the actual underlying cause(s) in these acyclic examples, related studies have shown that the steric demand of the oxido-group can gain considerably greater importance when cyclic systems are involved. Thus, alcohol 14[''] isomerizes by way of 15 to 16, avoiding in the process that transition state option involving exo C-C bond formation with axial oxido-group orientation. In contrast, stereoisomer 171181 must project the alkoxide group axially as in 18 to arrive at 16. This less favorable state of affairs allows for the competitive formation of 20 via 19. Therefore, a change in relative carbinol configuration can have significant impact on product distribution.

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