Synthesis and Properties of Phospha[5]helicenes Bearing an Inner-Rim Phosphorus Center.

Org Lett

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences , Nanyang Technological University, Singapore 637371 , Singapore.

Published: May 2019

AI Article Synopsis

  • New phospha[5]helicene derivatives have been created by combining phosphole and carbohelicene components, using a specific intermediate called 7-hydroxybenzo[b]phosphole oxide.
  • The process involves a one-pot multicomponent coupling method that allows for a targeted preparation of this intermediate.
  • Studies on the new compounds reveal a strong relationship between their phosphorous-centered chirality and overall helical structure, including their ability to easily switch between different forms in a solution.

Article Abstract

New phospha[5]helicene derivatives featuring angular fusion of phosphole and carbohelicene moieties have been synthesized using 7-hydroxybenzo[ b]phosphole oxide as a key intermediate, which can be regioselectively prepared through one-pot multicomponent coupling. The structural behavior of the present phospha[5]helicene oxide, sulfide, and gold complex in the solid and solution states, along with DFT calculations, demonstrated close correlation between the P-centered chirality and the helical chirality as well as facile helicity inversion and equilibrium between the diastereomers in solution.

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http://dx.doi.org/10.1021/acs.orglett.9b00955DOI Listing

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