Geometrical remote steric effects in 4,5-disubstituted-9,10- dihydrophenanthrenes: Expansion of prestrained C9-C10 bond in di(spiroacridan) derivatives

Kazuhisa Wada; Takashi Takeda; Hidetoshi Kawai; Ryo Katoono; Kenshu Fujiwara; Takanori Suzuki

doi:10.1246/cl.130502

Geometrical remote steric effects in 4,5-disubstituted-9,10- dihydrophenanthrenes: Expansion of prestrained C⁹-C¹⁰ bond in di(spiroacridan) derivatives

Kazuhisa Wada, Takashi Takeda, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Takanori Suzuki

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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 1c-1e 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.

Original language	English
Pages (from-to)	1194-1196
Number of pages	3
Journal	Chemistry Letters
Volume	42
Issue number	10
DOIs	https://doi.org/10.1246/cl.130502
Publication status	Published - 2013

ASJC Scopus subject areas

Chemistry(all)

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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 1c-1e is expanded from 1.634(2) to 1.649(3)-1.652(6) {\AA}, 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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AU - Wada, Kazuhisa

AU - Takeda, Takashi

AU - Kawai, Hidetoshi

AU - Katoono, Ryo

AU - Fujiwara, Kenshu

AU - Suzuki, Takanori

PY - 2013

Y1 - 2013

N2 - 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 1c-1e 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.

AB - 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 1c-1e 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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Geometrical remote steric effects in 4,5-disubstituted-9,10- dihydrophenanthrenes: Expansion of prestrained C⁹-C¹⁰ bond in di(spiroacridan) derivatives

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