TY - JOUR
T1 - Cycloaddition of 1-Azirines to 1,3-Diphenylisobenzofuran and Rearrangement of the Adducts
AU - Hassner, Alfred
AU - Anderson, David J.
PY - 1974/7/1
Y1 - 1974/7/1
N2 - 1-Azirines 1 and 1,3-diphenylisobenzofuran (2) react smoothly and efficiently in refluxing toluene to afford the simple 1:1 adducts 3, possessing the exo configuration. Two of the adducts, 3a and 3b, were found to rearrange in the presence of neutral alumina, to give the epoxybenzo-2H-azepines 20a and 20b. Chemical reactions (water, alcohol, LiAlH4) of the adducts 3 generally involved initial opening of the oxido bridge in a regiospecific manner. When more vigorous conditions were used, rupture of the aziridine ring usually followed.
AB - 1-Azirines 1 and 1,3-diphenylisobenzofuran (2) react smoothly and efficiently in refluxing toluene to afford the simple 1:1 adducts 3, possessing the exo configuration. Two of the adducts, 3a and 3b, were found to rearrange in the presence of neutral alumina, to give the epoxybenzo-2H-azepines 20a and 20b. Chemical reactions (water, alcohol, LiAlH4) of the adducts 3 generally involved initial opening of the oxido bridge in a regiospecific manner. When more vigorous conditions were used, rupture of the aziridine ring usually followed.
UR - http://www.scopus.com/inward/record.url?scp=0000256924&partnerID=8YFLogxK
U2 - 10.1021/jo00928a011
DO - 10.1021/jo00928a011
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AN - SCOPUS:0000256924
SN - 0022-3263
VL - 39
SP - 2031
EP - 2036
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -