synthesis of bis (1-methyl-2-octynyl) etherbis(1-methyl-2-octynyl)醚的合成.pdfVIP

synthesis of bis (1-methyl-2-octynyl) etherbis(1-methyl-2-octynyl)醚的合成.pdf

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synthesis of bis (1-methyl-2-octynyl) etherbis(1-methyl-2-octynyl)醚的合成

Molbank 2009, M612 OPEN ACCESS molbank ISSN 1422-8599 /journal/molbank Short Note Synthesis of Bis (1-Methyl-2-octynyl) Ether David Díaz Díaz * and Víctor S. Martín Instituto Universitario de Bio-Orgánica “Antonio González”, Universidad de La Laguna, Avda, Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain * Author to whom correspondence should be addressed; E-Mail: DDDchemistry@ Received: 18 July 2009 / Accepted: 4 August 2009 / Published: 5 August 2009 Abstract: The synthesis of bis (1-methyl-2-octynyl) ether using two secondary alcohols under Nicholas reaction conditions is reported. The reaction is possible due to a catalytic participation of the Lewis acid when the nucleophilic alcohol is protected as a THPO-ether. Keywords: Nicholas reaction; cobalt; alkyne complexes The reaction of a dicobalt octacarbonyl-stabilized propargylic cation with a nucleophile, followed by oxidative demetallation to yield propargylated products (Nicholas reaction) has been proved to be a versatile synthetic tool in organic synthesis [ 1–4]. This process has been used to prepare both symmetrical and unsymmetrical propargylic ethers [5], which are particularly important due to the wide range of functional group interconversions that the triple bond permits [6]. Nevertheless, when the propargylic cation is formed using a secondary alcohol, only primary alcohols are effective as nucleophiles to yield the correspo

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