Preparation of Highly Hindered Polyenes with tert-Butyl Groups in Internal Positions

Authors

  • Dr. Markus Betz,

    1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany), Fax: (+49) 531-391-5388
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  • Prof. Dr. Henning Hopf,

    Corresponding author
    1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany), Fax: (+49) 531-391-5388
    • Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany), Fax: (+49) 531-391-5388
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  • Prof. Dr. Ludger Ernst,

    1. NMR-Laboratorium der Chemischen Institute der Technischen Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany), Fax: (+49) 531-391-8192
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  • Prof. Dr. Peter G. Jones,

    1. Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig (Germany), Fax: (+49) 531-391-5387
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  • Prof. Dr. Yoshio Okamoto

    1. EcoTopia Science Institute, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603 (Japan), Fax: (+81) 52-789-3188
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  • Highly hindered olefins and polyolefins, XVI. Part XV: ref. 1.

Abstract

The conjugated tetraenes 3 and 4 ac have been prepared and shown to possess an orthogonal structure. This was not only demonstrated by their spectroscopic properties and X-ray structural analysis of solid representatives (e.g., 4 ac) but also by the resolution of these chiral compounds by GC and HPLC chromatography using various chiral selector systems. The chemical behavior of the typical tetraene 4 a has been studied using bromination, hydrogenation, epoxidation, and photo equilibration reactions.

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