By Regitz M., Felcht U.-H., Gallenkamp B. (eds.)
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Extra resources for Houben-Weyl Methoden der organischen Chemie vol.E2 Organic Phosphorus Compounds II
W. George, M. Poliakoff, “Vibrational Spectroscopy”; NMR: J. W. Rathke, R. J. Klingler, R. E. Gerald H, D. E. Fremgen, K. Woelk, S. Gaemers, C. J. : C. R. Yonker, J. C. Linehan, J. L. Fulton, “UV, EPR, X-ray, and Related Spectroscopic Techniques”, (Eds. P. G. Jessop, W. Leitner), In Chemical Synthesis Using Supercritical Fluids, Wiley–VCH, Weinheim, Chapter 3, 1999, pp. 147–212. 15. J. M. DeSimone, Z. Guan, C. S. Elsbernd, “Synthesis of Fluoropolymers in Supercritical Carbon Dioxide”, Science 1992, 257, 945–947.
The 5-exo-trig process is kinetically more favored over the 6-endo-trig cyclization which gives the more stable six-membered rad- Epilogue 23 Figure 15. Silane-mediated free-radical carbonylations of alkyl halides in scCO2 ical. Prior to reaction with a silane, the initially formed exocyclic radical slowly isomerizes to the ring-expanded isomer in a solvent cage. Under a lower CO2 pressure condition with a weaker cage effect, the contribution of the kinetically favored exocyclic radical is increased.
However, thanks to the technique of fluorous solid-liquid extraction, there is surprisingly broad latitude here. Fluorous Synthesis Techniques 31 Figure 7. Fluorous tin reactions with separation by solid-liquid extraction Our initial work used fluorous solid phase extraction mainly as a convenience.  All these reagents are sufficiently soluble in organic solvents, so no fluorous or hybrid solvents or cosolvents are needed to conduct reactions. However, due to the low fluorous/ organic partition coefficients of these reagents, repeated extractions (as many as 8–20) can be needed in liquid-liquid extractive workups.