Format:
Online-Ressource
ISSN:
1099-0690
Content:
Abstract: The electron‐accepting sulfonyl group exhibits a strong acidifying influence on neighboring α‐H atoms. The Julia and related olefinations are based on this effect. Here a surprising reversal in the metalation selectivity of branched alkyl aryl sulfones is described. Such sulfones were found to initially undergo directed ortho‐metalation with good regioselectivity, despite having a more acidic α‐H atom. The structure of the alkyl unit profoundly, but predictably, influences the regioselectivity of the attack of the base. In β‐ and γ‐branched ortho‐(alkylsulfonyl) aryllithiums a transmetalation to the α‐carbanion proceeds only upon warming. Correspondingly generated ortho‐ or α‐carbanions were then selectively applied thus permitting access to synthetically interesting compound classes.
In:
volume:2014
In:
number:7
In:
year:2014
In:
pages:1461-1476
In:
extent:16
In:
European journal of organic chemistry, Weinheim : Wiley-VCH Verl., 1998-, 2014, Heft 7 (2014), 1461-1476 (gesamt 16), 1099-0690
Language:
English
DOI:
10.1002/ejoc.201301553
URN:
urn:nbn:de:101:1-2023011407042367692835
URL:
https://doi.org/10.1002/ejoc.201301553
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023011407042367692835
URL:
https://d-nb.info/1278166416/34
URL:
https://doi.org/10.1002/ejoc.201301553
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