By Alan R. Katritzky
(from preface)The 7th quantity of Advances in Heterocyclic Chemistry comprises surveys of 4 teams of heterocyclic compounds; furans (P. Bosshard and zero. H. Eugster), dithiolium salts (H. Prinzbach and E. Futterer), 1,3,4-oxadiazoles (A. Hetzheim and okay. Mockel), and diquinolylme-thanes (G. Scheibe and E. Daltrozzo). additional chapters take care of functions of mass spectrometry to heterocycles (G. Spiteller), a space which has increased very quickly of past due, and the halogenation of heterocycles (J. J. Eisch). ultimately, a precis is given of stories within the heterocyclic box, categorised via topic (A. R. Katritzky and S. M. Weeds), which it truly is was hoping might be of suggestions in literature surveys.Suggestions are welcomed for contributions to extra volumes; they need to be within the type of a quick synopsis.Thanks are as a result of Editorial Board, the publishers, and the authors for his or her cooperation.
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Extra resources for Advances in Heterocyclic Chemistry
E. QUALITATIVE LOCALIZATION TREATMENT OF HETEROCYCLIC HALOGENATION 1. Monocyclic Systems I n broad terms, the sites of heterocyclic halogenation follow the relative stabilities of the possible tetrahedral transition states, as assessed by a qualitative resonance treatment. For electrophilic attack the more stable transition states will be those permitting maximum positive charge dispersal, while disrupting a minimum of aromatic sextets and avoiding the positioning of the charge on electronegative heteroatoms.
Gewald, J . Prakt. Chem. 20, 244 (1963). 11. 2 The benzylcarbonium-sulfonium salt (23) evidently lacks the stability and integrity of the benzo-l,2-dithiolium salt ( ~ O C ) ,which is also a benzylcarbonium-sulfonium salt, &s shown by two of its canonical structures. Thus the benzylcarbonium ion character common to 20c and 23, with additional stabilization by the adjacent sulfur atom, is not sufficient to explain the stability of the ion 20c. ) of the dark-green tetrathiotetracene (i)37 which a t least formally can be looked on as a bis-1,2-dithiolium system.
Chem. SOC. 84, 2941 (1962). 24 D. Leaver, D. M. McKinnon, and W. A. H. Robertson, J . Chem. SOC. p. 32 (1965). 11. 25 (19) + R&HXY SCHEME 3 Suitable oxidizing agents include bromine (in benzene) and sulfuryl chloride (in ether/glacial acetic acid). The scope of this method has not yet been fully explored, and appears t o be capable of further modification and expansion. Though laborious in comparison with other routes, it makes possible the preparation of certain 1,%dithiolium salts that cannot be obtained, for example, by the extremely simple Klingsberg method (Section 11,A, 2,b).
Advances in Heterocyclic Chemistry by Alan R. Katritzky