By A. R. & Boulton, A. J. [Eds]. Katritzky
(from preface)Volume thirteen of this serial e-book contains six chapters of which 4 take care of basic bills of compound periods: 1-azirines (F. W. Fowler), phenanthridincs (B. R. T. Keene and P. Tissington), tri-thiapentalenes (N. Lozac'h), and heterocyclic fcrrocenes (F. D. Popp and E. B. Moynahan). the opposite chapters are all for specific points of the chemistry of teams of heterocycles: the tautomerism of purines (B. Pullman and A. Pullman) and quantitative facets of the electrophilic substitution reactions of five-membercd jewelry (G. Marino).
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 13
N a u k S M R , Otd. Khim. Nauk 1997 (1962);Chem. Abstr. 58, 9132 (1963). 106 T. I. Bieber and M. Y . Dorsett, J . Org. Chem. 29, 2028 (1964). lo7 M. Hadlington, B. W. Rockett, and A. Nelhans, J . Chem. SOC. C 143641967). 105 F. D. POPP AND E. B. MOYNAHAN 24 [Sec. A. acid,lo8 while 109 was also obtained in addition to 2-(ferrocenylmethy1)cyclohexanone from 107 and N-cyclohexenylpyrrolidine in wet acetonitrile. l'~ The asymmetric lithiation has been discussed. of 1-ferrocenylmethyl-2-methylpiperidine The piperidine derivative (111) has been reportedlog from the reaction of piperidine and 112 in acetic acid with sodium tetraphenylborate.
60, 9309 (1964). 79J. W . Huffman, L. H. Keith, and R. L. Asbury, J . Org. Chem. 30, 1600 (1965). 80 A. N. Nesmeyanov, V. A. Sazonova, and A. V. Gerasimenko, Dokl. Akad. NaukSSSR 147, 634 (1962); Chem. Abstr. 58,9133 (1963). 81 K. Schlogl and M. Fried, Monatsh. Chern. 94, 537 (1963). 77 Sec. 1 HETEROCYCLIC FERROCENES 19 cenylenediboronic acid and copper carbonate were heated in pyridine. Irradiation of the methiodide of 86 gave an 84% yield of N-methyl2-cyclopentadienylene-1,2-dihydropyridine and some cyclopentadiene.
Miscellaneous 1 -Azirine Synthesis . IV. Reactions of 1-Azirines . A. Electrophilio Reagents . B. Nucleophilic Reagents . C. Cycloadditions . V. Summary . . . . . . . 45 46 48 48 51 60 62 63 63 69 74 76 I. Introduction Azirine is the term used to describe a three-membered heterocycle containing one nitrogen atom and one double bond. There are two isomeric azirines (1 and 2) which have been designated by ChernicaE Abstracts and “The Ring Index,” as 1H-and 2H-azirine, respectively. Due to some confusion in the literature using the “indicated hydrogen” nomenclature 2- and 1-azirine have been suggested as terms t o describe 1 and 2.
Advances in Heterocyclic Chemistry, Vol. 13 by A. R. & Boulton, A. J. [Eds]. Katritzky