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Sulfones as Chemical Chameleons: Versatile Synthetic Equivalents of Small‐Molecule Synthons
Author(s) -
Trost Barry M.,
Kalnmals Christopher A.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902019
Subject(s) - synthon , nucleophile , electrophile , chemistry , reactivity (psychology) , sulfone , radical , combinatorial chemistry , molecule , small molecule , organic chemistry , catalysis , medicine , alternative medicine , pathology , biochemistry
Sulfones are flexible functional groups that can act as nucleophiles, electrophiles, or even radicals. Changing the reaction conditions can completely alter the reactivity of a sulfonyl group, and as a result, molecules bearing multiple sulfones are versatile building blocks. This Review highlights the unique ability of 1,1‐ and 1,2‐bis(sulfones) to masquerade as a vast array of reactive synthons including methane polyanions, vinyl cations, and all‐carbon dipoles that would be difficult or impossible to access directly.