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Preparation of 1-Tosyloxy-4-Substituted-2-butenes Using Ag(I) Salts.


ABSTRACT: The trans-fluoro-2-butenyl group has been previously utilized as an N-substituent on several nortropanes for imaging the dopamine transporter with positron emission tomography. We report here a simplified and shorter synthesis of trans-1-tosyloxy-4-substituted-2-butenes using Ag(I) salts. This methodology was also applied to the synthesis of the cis-isomers. Furthermore, these procedures allow for the recovery of the majority of the Ag(I) ions.

SUBMITTER: Stehouwer JS 

PROVIDER: S-EPMC4542012 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Preparation of 1-Tosyloxy-4-Substituted-2-butenes Using Ag(I) Salts.

Stehouwer Jeffrey S JS   Goodman Mark M MM  

Tetrahedron letters 20150701 30


The <i>trans</i>-fluoro-2-butenyl group has been previously utilized as an <i>N</i>-substituent on several nortropanes for imaging the dopamine transporter with positron emission tomography. We report here a simplified and shorter synthesis of <i>trans</i>-1-tosyloxy-4-substituted-2-butenes using Ag(I) salts. This methodology was also applied to the synthesis of the <i>cis</i>-isomers. Furthermore, these procedures allow for the recovery of the majority of the Ag(I) ions. ...[more]

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