Non-Fiction Books:

New Aspects in Phosphorus Chemistry II

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Description

Strong non-ionic bases are highly advantageous as stoichiometric reagents and as catalysts in synthetic organic chemistry owing to side reactions that f- quently occur when ionic bases such as LDA or alkali metal alkoxides are employed. A second reason that non-ionic bases are frequently more useful in these applications is that such bases are often more soluble in less polar organic solvents,particularly at low temperatures. Thirdly,non-ionic bases can provide reactive naked or tightly associated deprotonated substrate anions that are s- bilized by the relatively large,poorly solvated cations formed by the protonated base. In such cations,extensive positive charge delocalization can occur. Prior to our work on pro-azaphosphatranes of type 1 (Scheme 1),the very strong n- ionic bases utilized for organic transformations were largely confined to the nitrogenous bases shown below (Scheme 2). Scheme 1 Scheme 2 4 J. G. Verkade 2 Uses of Strong Nonionic Nitrogen Bases 2. 1 Amines One of the earliest strong non-ionic bases to make its appearance was Proton Sponge and its derivatives [1] and these systems have been reviewed [2]. More recently Proton Sponge has been used in the palladium-catalyzed arylation of 2,3-dihydrofuran [3], and it also catalyzes Knoevenagel condensations of s- strates possessing activated methylene groups [4]. Recently the synthesis of the macrocyclic tetramine below (Scheme 3) was reported [5]. The encrypted nitrogens are very basic (pK ,24.
Release date NZ
November 27th, 2002
Audiences
  • Postgraduate, Research & Scholarly
  • Professional & Vocational
Contributors
  • Contributions by A.-M. Caminade
  • Contributions by H. Heydt
  • Contributions by J.-P. Majoral
  • Contributions by M. Mikolajczyk
  • Contributions by P. Balczewski
  • Contributions by R. Streubel
  • Contributions by S. Ito
  • Contributions by T.D. Nixon
  • Contributions by T.P. Kee
  • Edited by Jean-Pierre Majoral
Illustrations
X, 263 p.
Pages
263
Dimensions
155x235x10
ISBN-13
9783540440864
Product ID
5268002

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