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Synthesis and Reactions of Triptycenes and Their Derivatives

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Iptycenes Chemistry

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Abstract

In order to verify if the triptycyl (the analog of triphenylmethyl in which the three phenyl groups were united to a CH) free radical 1a should be more instable than the triphenylmethyl radical itself, Bartlett et al. (J Am Chem Soc 64:2649–2653, 1942) first synthesized triptycene 1 in a low total yield by a multistep route starting from the Diels–Alder addition reaction of anthracene and benzoquinone in 1942. Several years later, Bartlett et al. (J Am Chem Soc 72 (2):1003–1004, 1950) also reported the synthesis of 9-bromotriptycene (2) from the 9-bromoanthracene and benzoquinone according to the similar synthetic strategy. However, it was noted that the target compound 2 could be immediately afforded by the deamination of the diamine with NaNO2 in the presence of 50 % H3PO2 at − 3 °C.

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  1. Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China

    Chuan-Feng Chen & Ying-Xian Ma

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  1. Chuan-Feng Chen
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Correspondence to Chuan-Feng Chen .

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Chen, CF., Ma, YX. (2013). Synthesis and Reactions of Triptycenes and Their Derivatives. In: Iptycenes Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-32888-6_2

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