(3 + 3) Annulation of Nitroallylic Acetates with Stabilized Sulfur Ylides for the Synthesis of 2-Aryl Terephthalates

Satham, Lakshminarayana ; Namboothiri, Irishi N. N. (2018) (3 + 3) Annulation of Nitroallylic Acetates with Stabilized Sulfur Ylides for the Synthesis of 2-Aryl Terephthalates Journal of Organic Chemistry, 83 (16). pp. 9471-9477. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.8b00917

Related URL: http://dx.doi.org/10.1021/acs.joc.8b00917

Abstract

A novel (3 + 3) annulation approach has been developed for the synthesis of 2-aryl terephthalates from nitroallylic acetates and stabilized sulfur ylides. The 2-aryl terephthalates, which are also biaryls bearing a terephthalate moiety, are formed through a cascade of reactions such as a γ-selective SN2′ reaction, γ-selective intramolecular Michael addition, and two eliminations in the presence of Cs2CO3 in CH3CN at room temperature. The products are formal precursors of farnesyltransferase inhibitors and are also potential monomers in polymer chemistry.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
Keywords:Terephthalate; Annulations; Organic Compounds; Anions; Liquids.
ID Code:121320
Deposited On:14 Jul 2021 09:33
Last Modified:14 Jul 2021 09:33

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