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Synthesis of cage [4.4.2]propellanes and \({D_{3}}\)-trishomocubanes bearing spiro linkage

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Abstract

The synthesis of substituted cage [4.4.2]propellanes and \(D_{3}\)-trishomocubanes bearing spiro linkage have been assembled with the aid of Diels–Alder reaction and ring-rearrangement as key steps. Here, readily available 1,4-hydroquinone, isoprene, spiro[2.4]hepta-4,6-diene and spiro[4.4]nona-1,3-diene were used as starting materials. The unusual rearrangement of cage propellanes with zinc/acetic acid produced \(D_{3}\)-trishomocubanes in good yields.

Graphical Abstract

Several cage [4.4.2]propellanes and \(D_{3}\)-trishomocubanes have been assembled by Diels–Alder reaction (DA), [2+2] photocycloaddition, and acid-promoted rearrangement. Ring-rearrangement was observed in cage [4.4.2]propellane framework during the acid catalyzed reaction. Rearrangement approach provide new opportunities to construct unusual polycycles.

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Acknowledgements

We thank the Defence Research and Development Organisation (DRDO, NO. ARDB/01/1041849/M/1), New Delhi, for financial assistance and gratefully acknowledge Praj Industries for Pramod Chaudhari Chair Professorship (Green Chemistry). S. K. thanks the Department of Science and Technology (DST, NO. SR/S2/JCB-33/2010) for the award of a J. C. Bose fellowship and S. R. C. thanks University Grants Commission (UGC), New Delhi for the award of a research fellowship.

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  1. Department of Chemistry, Indian Institute of Technology-Bombay, Powai, India

    Sambasivarao Kotha & Subba Rao Cheekatla

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  1. Sambasivarao Kotha
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Correspondence to Sambasivarao Kotha.

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Kotha, S., Cheekatla, S.R. Synthesis of cage [4.4.2]propellanes and \({D_{3}}\)-trishomocubanes bearing spiro linkage. J Chem Sci 130, 171 (2018). https://doi.org/10.1007/s12039-018-1569-2

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