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Toda F, Tanaka K, Watanabe M, et al. Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes. J Org Chem. 1999;64(9):3102-3105doi: 10.1021/jo982010c.
Toda, F., Tanaka, K., Watanabe, M., Tamura, K., Miyahara, I., Nakai, T., & Hirotsu, K. (1999). Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes. The Journal of organic chemistry, 64(9), 3102-3105. https://doi.org/10.1021/jo982010c
Toda, Fumio, et al. "Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes." The Journal of organic chemistry vol. 64,9 (1999): 3102-3105. doi: https://doi.org/10.1021/jo982010c
Toda F, Tanaka K, Watanabe M, Tamura K, Miyahara I, Nakai T, Hirotsu K. Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes. J Org Chem. 1999 Apr 30;64(9):3102-3105. doi: 10.1021/jo982010c. PMID: 11674408.
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J Org Chem. 1999 Apr 30;64(9):3102-3105. doi: 10.1021/jo982010c.

Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes.

The Journal of organic chemistry

Fumio Toda, Koichi Tanaka, Masaki Watanabe, Kenichi Tamura, Ikuko Miyahara, Tadashi Nakai, Ken Hirotsu

Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama 790-8577, Japan, and Department of Chemistry, Faculty of Science, Osaka City University, Sugimoto-cho, Sumiyoshi-ku, Osaka 950, Japan.

PMID: 11674408 DOI: 10.1021/jo982010c

Abstract

The sterically bulky t-Bu-substituted derivatives of 1,1,2,2-tetraphenyl-3,8-dichlorobuta[b]naphthalene (5), trans-1,2-tert-butyl-1,2-diphenyl- (8) and 1,1-di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalene (12), were prepared. X-ray analysis of 8 and 12 at 150 K showed that C-C bonds of 8 and 12 are 1.686 and 1.729 Å, respectively. The latter bond length is longer than that of 1.720 Å in 5 and is the longest one reliably determined to date.

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