Inapplicability of the Antiperiplanar Lone Pair Hypothesis to C-P Bond Breaking and Formation in Some S-C-P(+) Systems.

@article{Graczyk1996InapplicabilityOT,
  title={Inapplicability of the Antiperiplanar Lone Pair Hypothesis to C-P Bond Breaking and Formation in Some S-C-P(+) Systems.},
  author={Piotr P. Graczyk and Marian Mikolajczyk},
  journal={The Journal of organic chemistry},
  year={1996},
  volume={61 9},
  pages={2995-3002}
}
Both C(2)-P bond breaking and formation in the S-C-P(+) system do not occur according to the antiperiplanar lone pair hypothesis. Experiments using 2-phosphonio derivatives of 5-tert-butyl-1,3-dithiane and cis-4,6-dimethyl-1,3-dithiane are against the participation of higher-energy boat conformers as reactive intermediates. The results obtained support a possibility of conformational adjustment in the course of the reaction. Stereoelectronic control of the C(2)-P bond breaking and formation… CONTINUE READING