S. Kiyooka, M. Tada, S. Kan
Sep 1, 1996
Citations
0
Influential Citations
9
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Bis(binaphtho)-22-crown-5 and bis(binaphtho)-22-crown-4, having bromoarylene moities on their rim, were prepared from (R)- and (S)-2,2′-dihydroxy-1,1′-binaphthyl. An acyclic diol, bridged by two (R)-binaphthyl moieties, underwent cyclization reaction with diethylene glycol ditosylate to afford the corresponding (R,R)-bis(binaphtho)-22-crown-5 in a good yield (69%). A one-pot cyclization reaction of (R)-2,2′-dihydroxy-1,1′-binaphthyl with 2,6-bis(bromomethyl)bromobenzene resulted in a good yield (45%) of (R,R)-bis(binaphtho)-22-crown-4, having two symmetrical bromoarylene units. In contrast to the cases started with (R)- and (S)-2,2′ -dihydroxy-1,1′-binaphthyl, the racemate in cyclization reactions did not give the corresponding crown products in the expected proportion.