Synthesis of semibullvalene derivatives via Co2(CO)8-mediated cyclodimerization of 1,4-dilithio-1,3-butadienes

Shaoguang Zhang; Ming Zhan; Qifeng Wang; Chao Wang; Wen-Xiong Zhang; Zhenfeng Xi

doi:10.1039/C3QO00019B

Synthesis of semibullvalene derivatives via Co₂(CO)₈-mediated cyclodimerization of 1,4-dilithio-1,3-butadienes

Shaoguang Zhang,^a Ming Zhan,^a Qifeng Wang,^a Chao Wang,^a Wen-Xiong Zhang^a and Zhenfeng Xi*^a^b

* Corresponding authors

^a Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, China
E-mail: zfxi@pku.edu.cn

Abstract

Co₂(CO)₈-mediated cyclodimerization of 1,2,3,4-tetrasubstituted 1,4-dilithio-1,3-butadienes readily afforded octa-substituted semibullvalenes. The X-ray crystal structure of 1,2,5,6-tetraethyl-3,4,7,8-tetraphenyl semibullvalene was determined to show an unsymmetrical, localized structure, which is in sharp contrast with the C₂ symmetrical structure of its tetramethyl analogue. In addition, this Co₂(CO)₈-mediated cyclodimerization was found to be dependent on the substitution pattern of 1,4-dilithio-1,3-butadienes. The 1,4-diphenyl dilithio compound gave its corresponding cyclooctatetraene derivative, while the dilithio reagent without substituents at its 1,4-positions afforded a cyclopentadienone [4 + 2] dimer.

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Publication details

The article was received on 25 Oct 2013, accepted on 14 Dec 2013 and first published on 28 Jan 2014

Article type: Research Article

DOI: 10.1039/C3QO00019B

Citation: Org. Chem. Front., 2014,1, 130-134

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Synthesis of semibullvalene derivatives via Co₂(CO)₈-mediated cyclodimerization of 1,4-dilithio-1,3-butadienes

S. Zhang, M. Zhan, Q. Wang, C. Wang, W. Zhang and Z. Xi, Org. Chem. Front., 2014, 1, 130
DOI: 10.1039/C3QO00019B
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Organic Chemistry Frontiers

Synthesis of semibullvalene derivatives via Co₂(CO)₈-mediated cyclodimerization of 1,4-dilithio-1,3-butadienes

Abstract

Supplementary files

Publication details

Synthesis of semibullvalene derivatives via Co₂(CO)₈-mediated cyclodimerization of 1,4-dilithio-1,3-butadienes

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