A Convenient Synthesis of Dibenzo[a,c]cyclooctene Based on Thioenol Ether Reduction

Article Article scientifique Lettre A Convenient Synthesis of Dibenzo[a,c]cyclooctene Based on Thioenol Ether Reduction eng 1993 author Lottaz Pierre-André 26598 author Edwards Timothy Richard 27910 author Mentha Yves Gabriel 31605 author Burger Ulrich 25497 639-642 10.1016/S0040-4039(00)61640-4 0040-4039 https://linkinghub.elsevier.com/retrieve/pii/S0040403900616404 9,10,11,12-Tetrahydrodibenzo[a,b]cyclooctane-9,12-diol (6) is found to be reluctant to double bond forming elimination. It gives a bridge ether (7) instead. The corresponding diketone (5) reacts with benzyl mercaptan to provide the bis-thioenol ether (8-a. The latter, upon treatment with Raney nickle, gives the desired title diene 1. An alternative approach to 1, based on repeated carbane addition to phenanthrene, is also presented. Intramolecular reductive coupling Desulfurization of thioenol ethers Axial chirality Carbene addition Dewey 540 Swiss National Science Foundation 20-32645.91 CH 36 Département de chimie organique 141 false Tetrahedron Letters 34 4 00a07af8-576a-4aa3-8694-24c8ab765bd3 Article (Published version) Restricted Lottaz_TL_199334639.pdf 2485365 application/pdf Vignette Public 1-s2.0-S0040403900616404-gr1.gif 3611 image/gif restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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A Convenient Synthesis of Dibenzo[a,c]cyclooctene Based on Thioenol Ether Reduction	Tetrahedron Letters			1993	197	0

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Edwards, Timothy Richard