TY - JOUR
T1 - Trapping of 1,2-benzo-1,3,4-cycloheptatriene as evidence for a strained cyclic allene structure
AU - Yildiz, Yasar Kemal
AU - Ozturk, Turan
AU - Balci, Metin
PY - 1999/7/23
Y1 - 1999/7/23
N2 - 8-bromo-6,7-dihydrobenzocycloheptene 16 and 9-bromo-6,7- benzocycloheptadiene 17 have been synthesized via a new and simple method, and their allene reactions were studied. Treatment of 16 with a base in the presence of DPIBF (diphenylisobenzofuran) gave the strained bicyclic allene 9, which underwent a cycloaddition reaction to yield 25 and 26. On the other hand, the reaction of the vinyl bromide 17 with a base, either in the presence or absence of DPIBF, resulted in the formation of 7H- benzocycloheptadiene 21, rather than the alkyne 22.
AB - 8-bromo-6,7-dihydrobenzocycloheptene 16 and 9-bromo-6,7- benzocycloheptadiene 17 have been synthesized via a new and simple method, and their allene reactions were studied. Treatment of 16 with a base in the presence of DPIBF (diphenylisobenzofuran) gave the strained bicyclic allene 9, which underwent a cycloaddition reaction to yield 25 and 26. On the other hand, the reaction of the vinyl bromide 17 with a base, either in the presence or absence of DPIBF, resulted in the formation of 7H- benzocycloheptadiene 21, rather than the alkyne 22.
UR - http://www.scopus.com/inward/record.url?scp=0033597976&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(99)00493-7
DO - 10.1016/S0040-4020(99)00493-7
M3 - Article
AN - SCOPUS:0033597976
SN - 0040-4020
VL - 55
SP - 9317
EP - 9324
JO - Tetrahedron
JF - Tetrahedron
IS - 30
ER -