Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Letter
Geometrical Remote Steric Effects in 4,5-Disubstituted-9,10-dihydrophenanthrenes: Expansion of Prestrained C9–C10 Bond in Di(spiroacridan) Derivatives
Kazuhisa WadaTakashi TakedaHidetoshi KawaiRyo KatoonoKenshu FujiwaraTakanori Suzuki
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2013 Volume 42 Issue 10 Pages 1194-1196

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Abstract

By attaching bulky substituents at the bay region of di(spiroacridan)-substituted dihydrophenanthrene 1a, the prestrained C9–C10 bond in the dihydrophenanthrene (DHP) skeleton of 1c1e is expanded from 1.634(2) to 1.649(3)–1.652(6) Å, 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 C4/C5 positions to cause the additional strain in the C9–C10 bond.

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© 2013 The Chemical Society of Japan
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