Phosphite-mediated conversion of benzaldehydes into stilbenes via umpolung through a dioxaphospholane intermediate

TETRAHEDRON LETTERS

卷:56

Article

Petersen, Johannes F.¹  Tortzen, Christian G.¹  Jorgensen, Frederik Praestholm¹  Parker, Christian R.¹  Nielsen, Mogens Brondsted¹ 

[1] Univ Copenhagen, Dept Chem, DK-2100 Copenhagen O, Denmark

关键词: Cruciform;    Dioxaphospholane;    Phosphite;    Stilbene;    Tetrathiafulvalene;   

DOI  :  10.1016/j.tetlet.2015.02.108

来源: Elsevier

【 摘 要 】

The phosphite-mediated coupling of two benzaldehydes into 2,2,2-triethoxy-1,3,2-dioxaphospholanes was investigated using C-13 NMR spectroscopy and was found to be very sensitive to the nature of the ortho/para substituents, and promoted by electron-withdrawing groups (EWGs). Stilbene-extended tetrathiafulvalenes were prepared by heating the intermediate dioxaphospholane, containing aldehyde substituents at para positions and ethynyl groups at ortho/meta positions, with 1,3-dithiol-2-thiones in P(OEt)(3). While EWGs promoted dioxaphospholane formation, electron-donating groups (EDGs), generated by conversion of the aldehydes into dithiafulvenes, promoted subsequent conversion into an alkene. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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