Regio‐ and Stereocontrolled Synthesis of (2R*,3R*,4R*)‐3,4‐Dichloro‐1,2,3,4,5,8‐hexahydronaphthalen‐2‐yl Acetate via Tandem SN2′ Reactions |
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| Authors: | Nurhan Horasan‐Kishali Ertan Sahin Yunus Kara |
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| Institution: | 1. Department of Chemistry, Faculty of Arts and Sciences, Atatürk University, TR‐25240 Erzurum;2. Author to whom inquiries concerning X‐ray structures should be directed. |
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| Abstract: | The hydroperoxy endoperoxide 3 , obtained by photooxygenation of isotetralin (= 1,4,5,8‐tetrahydronaphthalene; 1 ), was reduced with thiourea, and the resulting intermediate 4 was converted, after acetylation with acetyl chloride, to the interesting, double‐chlorinated acetate 5 in an unprecedented tandem reaction (Scheme 1). The structures and relative configurations of 3 and 5 were determined by NMR spectroscopy and by single‐crystal X‐ray‐diffraction analyses (Figs. 1 and 2, resp.). A mechanistic rationalization for the conversion of 4 to 5 is proposed (Scheme 2). |
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| Keywords: | Endoperoxides Tandem SN2′ reaction Acetyl chloride Chlorination X‐Ray crystallography Naphthalen‐2‐yl acetate NMR Spectroscopy |
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