By El Sayed H. El Ashry and Ahmed A. Kassem
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Additional info for Account of microwave irradiation for accelerating organic reactions
Saturated molecule is deformed. Other systems in which electromeric displacements become important include a carbon-carbon double bond, POLARIZABILITY OF UNSATURATED SYSTEMS C: :C [Approximate electron distribution 29 in the resting state] ee e HH C:C | [Form which becomes more important as a proton approaches] | a carbon-carbon conjugated system, ::C:C::C | H+ | [Approximate electron distribution in the resting state] | 9 C:C:C::C [Forms which become more important as a proton approaches] -C:C::C:C and a carbon-halogen conjugated system, [Resonance forms which are impor- C:C::C1: C::C:C1: tant in resting state] H e ^ H C:C: || [Form which becomes more important as a proton :C1: " .
71, 3513 (1949). 27 Taylor and Bakor, Sidgwick's Organic Chemistry of Nitrogen, p. 362, Oxford University Press, London, England, 1942. CARBONIUM ION REARRANGEMENTS CH 2 :N=N: 53 cn 2 e CH 2 OGJ XLVIII XLIX case the epoxide is formed; in the second, the completely polarized form of the next higher homolog of the cyclic kotone results. It is interesting that in most cases the yield of kctone is greater than that of the epoxide. Wolff Rearrangement. One of the steps in the Arndt-Eistert synthesis for the preparation of an acid from its preceding homolog 28 involves the conversion of a diazo methyl ketone into an acid derivative.
THE FORMATION OF CARBONIUM IONS' the addition of acids to unsaturated compounds. \-j 'c was of of the doubiu in out the discussion bonds polarizability (p. pointed 28), tlie presence of a proton displaces the normal position of tiie shared electrons comprising a multiple bond in the resting state so that Ihe bond assumes a more polarized form. Whenever an unsalurated compound, (1) By then, is dissolved in a proton donating solvent, equilibria like are established: ve n, C::O: " + H 7 or 3 - COH " * 1, 2, (1) I I r> C:::N + H ^=^ C=N H (2) H r* C::C f- H -;; ^ I O C (3) Similarly, for an electronically deficient molecule such aa chloride we have the equilibria 4, 5, or 6: alumiuum (4) C:::N + A1-C1 ^te -0=N-A1-C1 (5) Cl Cl 01 I Al ji^jk A Cl - * Cl e Al Cl (6) I -rr In each case the species formed contains a carbon atom with only 1 Whitmore, Ind.
Account of microwave irradiation for accelerating organic reactions by El Sayed H. El Ashry and Ahmed A. Kassem