Synthesis of certain [8](2,5)heterophanes

✍ Scribed by H. Nozaki; T. Koyama; T. Mori; R. Noyori

• Book ID: 104222905
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 104 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89715-4

✦ Synopsis

We wish to record a synthesis of novel 8heterophanes starting from 1,4oyolododeoanedione (I) which is readily accessible from oyolododecanone (1). Dehydration of the diketone I by treating with a mixture of phosphorus pentoxide and ethanol (2) at 80' for 1 hr gave 8furanophane (II), b.p. 104-106'/11 mm, in an 81% yield. IR spectrum (neat) showed characteristio bands at 5095 (-CH-), 1570 (C=C), 1020 (COC) and 780 cm-l (2,5_disubstituted furan), while UV maximum (n-hexane) occurred at 225 mp (log E 3.91). Treatment of I with ammonium carbonate at 100-120" for 2 hr yielded crystalline 6pyrrolophane (III), m.p. 154-154.5' (from n-hexane), in an