By Dieter Hellwinkel (auth.)
Content material: Penta- and hexáorganyl derivatives of the most staff 5 parts / D. Hellwinkel - Enantioselective synthesis of nonproteinogenic amino acids / U. Schöllkopf -- chosen issues of the Wittig response within the synthesis of common items / H.J. Bestmann, O. Vostrowsky -- commercial functions ot the Wittig response / H. Pommer, percent. Thieme -- attitude strained cycloalkynes / A. Krebs, J. Wilke
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Day, R. , Holmes, R. : ibid. 19, 3609 (1980) 85. Muetterties, E. , Schunn, R. A. : Quarterly Reviews 20, 245 (1966) 86. Holmes, R. , Deiters, J. : J. Amer. Chem. Soc. 99, 3318 (1977) Holmes, R. R. : Accounts Chem. Res. 12, 257 (1979) 87. Sheldrick, W. : Top. Curr. Res. 73, 1 (1978) 88. Holmes, R. R. : J. Amer. Chem. Soc. 100, 433 (1978) 89. Luckenbach, R. : Dynamic Stereochemistry of Pentacoordinated Phosphorus and Related Elements, Thieme, Stuttgart 1973 90. Hamilton, W. C. et al. : J. Amer. Chem.
A Model for Calculating Conformational Energies in Pentacoordinate Phosphorus Compounds. R. R. Holmes, J. Am. Chem. Soc. 100, 433 (1978). Pentacoordinate Phosphoranes in Synthesis. K. Burger, in Organophosphorus Reagents in Organic Synthesis, Edit. J. I. G. Cadogan, p. 467, Academic Press, London, 1979. Structure o f Cyclic Pentacoordinated Molecules o f Main G r o u p Elements. R. R. Holmes, Accounts Chem. Res. 12, 257 (1979). The Polytopal Rearrangement at Phosphorus, F. H. Westheimer in Rearrangements in G r o u n d and Exited States, Vol.
Several reaction sequences can be given for the generation of 171, the simplest one, starting with a reduction process by the aryllithium, not even including as intermediates the desired species 167 and 168. The initial orange color, observed in these reactions at --70 °C, points to an at least peripheral occurence of the tetracoordinated antimonate anion 170, which seems to be much less viable then the analogous and also intensely colored phosphate and arsenate complexes 79 and 145. Equally, the inaccessibility of 167 and 168 in these reactions points to a considerably reduced stability with respect to analogous phosphorus and arsenic species, which again is explained by the higher ring strains caused by the larger antimony central atom t3s) When bis-2,2'-biphenylylenephenylstiborane (150) is treated with lithium aluminum hydride in diethyl ether or better in tetrahydrofurane, a deep red solution results, from which after addition of iodine good yields of 2,2'-biphenylyleneiodostibine (175) can be isolated 137) Again a nucleophilic substitution, here by the hydride ion, is involved, leading first to the carbanionic hydridostiborane 172 (or the 47 I CT • c~ c~ P~ ~D Penta- and HexaorganylDerivativesof the Main Group Five Elements corresponding ate-complex), which decomposes rapidly to stibine 173 and 2-1ithiobiphenyl.
