A Very Simple Synthesis of Annelated λ3‐ and λ5‐Phosphanaphthalenes. Issue 17 (3rd May 2017)

• Record Type: Journal Article
• Authors: Zhang, Lujun; Yang, Feichao; Tao, Guanyu; Qiu, Liqi; Duan, Zheng; Mathey, François
• Is Part Of: European journal of inorganic chemistry. Issue 17(2017)
• Page Start: 2355
• Page End: 2362
• Publication Date: 2017-05-03
• Subjects: Phosphorus -- Heterocycles -- Fluorescence -- Synthetic methods; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejic.201700011
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract : ortho ‐Phosphinobenzonitriles (or thieno, pyridino analogues) react with dimethyl acetylenedicarboxylate between –78 °C and room temperature to give annelated λ 5 ‐phosphanaphthalenes. Interesting variations of the fluorescence properties are observed when the R substituents at P are alkyl or aryl. When R = t Bu, the thermolysis of the product affords the corresponding trivalent phosphanaphthalene. Abstract : The reaction of dimethyl acetylenedicarboxylate with (2‐cyanophenyl)phosphines results in substituted λ 5 ‐phosphanaphthalenes. When the R substituents at the phosphorus atom are tert ‐butyl, thermolysis affords the corresponding λ 3 ‐phosphanaphthalene. The P=C double bond of this product is activated by CO2 Me. Interesting variations of the spectral properties occur when changing the substituents at the phosphorus atom.