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Issue 5, 2018
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Reversible addition of terminal alkenes to digermynes†‡

Tomohiro Sugahara,a   Jing-Dong Guo,a   Takahiro Sasamori, ORCID logo *b   Shigeru Nagasec  and  Norihiro Tokitoh ORCID logo a  
Author affiliations

* Corresponding authors

a Institute for Chemical Research, Kyoto University, Gokasho Uji, Kyoto 611-0011, Japan

b Graduate School of Natural Sciences, Nagoya City University, Yamanohata 1, Mizuho-cho, Mizuho-ku, Nagoya, Aichi 467-8501, Japan
E-mail: sasamori@nsc.nagoya-cu.ac.jp

c Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo-ku, Kyoto 606-8103, Japan

Abstract

Stable digermynes with sterically demanding Bbt (Bbt = 2,6-[CH(SiMe3)2]2-4-[C(SiMe3)3]-C6H2) or Tbb (Tbb = 4-tBu-2,6-[CH(SiMe3)2]2-C6H2) groups underwent [2+2] cycloadditions with terminal alkenes to give the corresponding 1,2-digermacyclobutenes. In the case of the Bbt-substituted digermyne, the reaction was reversible at room temperature, i.e., the 1,2-digermacyclobutene (Ge(II) species) is susceptible to a facile reductive elimination that affords the corresponding digermyne (Ge(I) species) and the alkene.

Graphical abstract: Reversible addition of terminal alkenes to digermynes

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Supplementary files

Article information

https://doi.org/10.1039/C7CC08555A
Submitted
07 Nov 2017
Accepted
11 Dec 2017
First published
11 Dec 2017
Chem. Commun., 2018,54, 519-522
Article type
Communication
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Reversible addition of terminal alkenes to digermynes

T. Sugahara, J. Guo, T. Sasamori, S. Nagase and N. Tokitoh, Chem. Commun., 2018, 54, 519
DOI: 10.1039/C7CC08555A

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