4.3 Article

Geometrical Remote Steric Effects in 4,5-Disubstituted-9,10-dihydrophenanthrenes: Expansion of Prestrained C9-C10 Bond in Di(spiroacridan) Derivatives

Journal

CHEMISTRY LETTERS
Volume 42, Issue 10, Pages 1194-1196

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/cl.130502

Keywords

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Funding

  1. MEXT, Japan
  2. JSPS [23-4640]
  3. Grants-in-Aid for Scientific Research [11J04640, 24750032, 23655024] Funding Source: KAKEN

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By attaching bulky substituents at the bay region of di(spiroacridan)-substituted dihydrophenanthrene la, the prestrained C-9-C-10 bond in the dihydrophenanthrene (DHP) skeleton of le le is expanded from 1.634(2) to 1.649(3)-1.652(6)angstrom, which demonstrates the bond expansion through remote steric effects. Twisting deformation of the DHP skeleton is the key to transfer the steric bulkiness from the C-4/C-5 positions to cause the additional strain in the C-9-C-10 bond.

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