By Saul E. (editor) Patai
Content:
Chapter 18 contemporary advancements on nitrile oxides, nitrile sulphides and nitrile selenides (pages 737–804): Giorgio Bianchi, Remo Gandolfi and Paolo Grunanger
Chapter 19 Conformation of cyano and isocyano compounds (pages 805–834): C. A. Kingsbury
Chapter 20 contemporary advances in isocyanide chemistry (pages 835–887): H. M. Walborsky and M. P. Periasamy
Chapter 21 Complexation of aryldiazonium ions via polyethers (pages 889–915): Richard A. Bartsch
Chapter 22 Poly(diacetylenes) and polyyne polymers containing transition?metal atoms on the whole chain (pages 917–980): William D. Huntsman
Chapter 23 Cyclodimerization of alkynes and reactivity of aluminium halide ? complexes of cyclobutadienes (pages 981–1013): Hepke Hogeveen and Douwe M. Kok
Chapter 24 constitution of triple?bonded molecules (pages 1015–1034): J. B. Moffat
Chapter 25 NMR spectra of acetylenes (pages 1035–1056): D. G. Morris
Chapter 26 guidance and artificial functions of cyano compounds (pages 1057–1303): Alexander J. Fatiadi
Chapter 27 common and theoretical homes of triple?bonded molecules (pages 1305–1343): J. B. Moffat
Chapter 28 fresh advances within the synthesis of triple?bonded teams (pages 1345–1390): Klaus Friedrich
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Additional info for Triple-Bonded Functional Groups: Volume 2 (1983)
Sample text
This type of electronic effect was also invoked to explain the syrz -anti selectivity of the LU nitrile oxide controlled reactions of compounds 78'51,152. In norbornadienes 78a-c the effect of the methano bridge prevails, while in 78d and 78e the dominant conjugative entity was suggested to be the tetrasubstituted double bond with a consequent larger HO extension (higher sr-electron density) anti to the ethano and propano bridge, respectively, in agreement with experimental results. Syn-anti ratio values for adducts 79 and 80 have been shown to be dependent on reaction conditions.
This finding raises the mechanistically interesting possibility that along the reaction path leading to 91 and 92 there is a dipolar intermediate of the type 94. (94) Another notewoTthy aspect of the reactions of Scheme22 is the site selectivity change induced by the irontricarbonyl group. 3). A similar behaviour was observed previously for tropone and tropone-irontricarbonyi161. Site selectivity (and regioselectivity) in the reactions of allenes with nitrile oxides has also attracted the interest of r e s e a r c h e r ~ l ~ ~The , ’ ~ salient ~,~~~ data .
The anti methano bridge adducts are always dominant but also worth noting is the ratio between the two isomeric syn adducts. In fact, the most hindered of the two possible syiz attacks is the only o r the preferred reaction path chosen by the 1,3-dipole. syn adducts Y PhCOO t-BuO OH A( %) 13 23 12 anti adducts B(%) C( %) D(%) 6 41 0 29 40 40 59 0 37 Total yield (%) 76 75 66 SCHEME 18 Further examples of dominant anti methano bridge addition to norbornadiene systems are found in the HO-dipole controlled reactions of benzonitrile oxide with electron-poor polychloronorbornadienes which give anti (81) and syn (82) ad duct^'^^.
