Synthesis of Stable Tri- and Tetra-Substituted [3]Dendralenes with an Allylsilane as Integral Component

Rekha Singh, Gonna Somu Naidu, Sunil K. Ghosh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A novel route to functionalized [3]dendralenes with an allylsilane as integral component has been developed. The key step involves a dimethylsulfonium methylide mediated olefination of appropriately substituted silylmethylethenylidene phosphonoacetate followed by Horner–Wadsworth–Emmons reaction with aromatic aldehydes. The tri- and tetra substituted [3]dendralenes are stable towards self Diels–Alder cyclodimerization which can be attributed to stereoelectronic effect of the silylmethyl group favoring for an unreactive conformation.

Original languageEnglish
Pages (from-to)619-625
Number of pages7
JournalProceedings of the National Academy of Sciences India Section A - Physical Sciences
Volume86
Issue number4
DOIs
StatePublished - 1 Dec 2016
Externally publishedYes

Keywords

  • Allylsilane
  • Conformation
  • Dimethylsulfonium methylide
  • Olefination
  • Stable [3]dendralenes

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