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Synthesis of [10]heterophanes using a ring enlargement reaction

✍ Scribed by Ferrid Hadj-Abo; Stefan Bienz; Manfred Hesse

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 596 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85341-2

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✦ Synopsis

The ring enhugcmaaof 2-nkwyclododccanone (1, n = 1) to methyl 2-hyd~oxy-5-ni~mcyclo~ carboxyiate (4, n = 1) via 12-hydroxy-l-nit&iiyslo[9.3.l]pcnmdccaw-12-one (2. n = 1) delivcaed after fintha tmnsfcnmations in good yield cycle 1 Pdione (12). Treatment of this compound with paw-toluew sulfonic acid et a Dean-stark wata hap affonw [lOl(2J)furanophane (2O).Inpmsalceofa orofaprimalyamine.thenspective 10pyrrolophanes 15-19 wit obtained. The azresponding ppiuation of [101(2,5)tbiopbenopbene (21) by action of sevaal sulfuring reagents on 12. however. was less succe&id. 0nly small amounts of impme 21 wcaeobtaiwd.

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