Synthesis of 1,3-Dehydroadamantanes Possessing Alkyl, Phenyl, and Alkoxy Substituents by Intramolecular Wurtz-Type Coupling Reaction of 1,3-Dibromoadamantanes

Sotaro Inomata; Yusuke Harada; Yuya Nakamura; Taisuke Nakamura; Takashi Ishizone

doi:10.1055/s-0033-1338554

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(24): 3332-3340
DOI: 10.1055/s-0033-1338554

feature article

Synthesis of 1,3-Dehydroadamantanes Possessing Alkyl, Phenyl, and Alkoxy Substituents by Intramolecular Wurtz-Type Coupling Reaction of 1,3-Dibromoadamantanes

Sotaro Inomata

Department of Organic and Polymeric Materials, Tokyo Institute of Technology , 2-12-1-S1-13 Ohokayama, Meguro-ku, Tokyo 152-8552, Japan eMail: tishizon@polymer.titech.ac.jp

,

Yusuke Harada

Department of Organic and Polymeric Materials, Tokyo Institute of Technology , 2-12-1-S1-13 Ohokayama, Meguro-ku, Tokyo 152-8552, Japan eMail: tishizon@polymer.titech.ac.jp

,

Yuya Nakamura

Department of Organic and Polymeric Materials, Tokyo Institute of Technology , 2-12-1-S1-13 Ohokayama, Meguro-ku, Tokyo 152-8552, Japan eMail: tishizon@polymer.titech.ac.jp

,

Taisuke Nakamura

Department of Organic and Polymeric Materials, Tokyo Institute of Technology , 2-12-1-S1-13 Ohokayama, Meguro-ku, Tokyo 152-8552, Japan eMail: tishizon@polymer.titech.ac.jp

,

Takashi Ishizone*

Department of Organic and Polymeric Materials, Tokyo Institute of Technology , 2-12-1-S1-13 Ohokayama, Meguro-ku, Tokyo 152-8552, Japan eMail: tishizon@polymer.titech.ac.jp

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Abstract

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Abstract

A series of highly strained [3.3.1]propellane derivatives, 1,3-dehydroadamantanes (DHAs) possessing alkyl, phenyl, and alkoxy substituents, such as 5-butyl, 5-hexyl, 5-octyl, 5-phenyl, 5-methoxy, 5-butoxy, 5,7-dimethyl, 5-ethyl-7-hexyl, 5,7-dibutyl-, 5-butyl-7-isobutyl, 5-butyl-7-hexyl, 5-butyl-7-phenyl, 5-butyl-7-methoxy, and 5-butoxy-7-butyl, were synthesized in several gram amounts. The 1,3-dibromoadamantanes carrying alkyl, phenyl, and alkoxy substituents were converted into the corresponding DHAs via the intramolecular Wurtz-type coupling reactions with lithium metal in THF in 21–81% yields.

Key words

1,3-dehydroadamantanes - 1,3-dibromoadamantanes - Wurtz coupling reaction - [3.3.1]propellanes

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Referenzen

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