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Improved Synthesis, Structure, and Cycloaddition Reaction of [3 4 ](1,2,4,5)Cyclophane
Author(s) -
Sentou Wakana,
Satou Teizi,
Yasutake Mikio,
Lim Chultack,
Sakamoto Youichi,
Itoh Tetsuji,
Shinmyozu Teruo
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199905)1999:5<1223::aid-ejoc1223>3.0.co;2-s
Subject(s) - cyclophane , cycloaddition , chemistry , stereochemistry , crystal structure , crystallography , organic chemistry , catalysis
The modified synthetic route to [3 4 ](1,2,4,5)cyclophane ( 3 ) provides gram quantities of this compound in fewer steps than the conventional routes. The cycloaddition of 3 with dicyanoacetylene ( 12 ) gave barrelenophane 13 , which was transformed into semibullvalenophane 15 on photoirradiation. This transformation ( 13 → 15 ) is in sharp contrast to the case of Boekelheide's [2 4 ]barrelenophane, where cyclooctatetraenophane is obtained. The X‐ray structural analyses of 3 , 13 , and 15 demonstrates their unique structures.