Study on the Mechanism of Formation of 1‐Methylheptyl Phenyl Ether by the Isourea Method |
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| Authors: | Eckehard Cuny Rolf Jaeger |
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| Institution: | 1. Institut für Organische Chemie der Technischen Universit?t Darmstadt, Petersenstr. 22, D‐64287 Darmstadt;2. Institut für Organische Chemie der Universit?t Kiel, Otto Hahn Platz 4, D‐24098 Kiel;3. Current address: Benedixweg 14, D‐21680 Stade. |
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| Abstract: | The formation of (1R)‐1‐methylheptyl phenyl ether from (2S)‐octan‐2‐ol via its isourea derivative (S)‐ 1 follows a borderline mechanism. The intermediacy of a carbocation (see (S)‐ 2 ) can be demonstrated (Scheme 1). However, the extremely high inversion of configuration and the olefinic by‐products are also indicative of an SN2 mechanism. |
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| Keywords: | Isourea N N′ ‐dicyclohexyl‐O‐(1‐methylheptyl)‐ Phenol Enantioselectivity X‐Ray crytallography |
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