TY  - JOUR
AB  - 10-Bromo-10-methyl-11-methylene[3.2]paracyclophane (3), available by bromination followed by dehydrobromination of 10,11-dimethyl[3.2]paracyclophane-10-ene (1), reacted with 1,4-diaza-[2.2.2]bicyclooctane (DABCO) by SN 1. Thermolysis of the quaternary ammonium salt 4 produced 10,11-dimethylene[3.2]paracyclophane (5). The Diels-Alder reactivity of 5 exceeds that of 1,4-diphenyl-1,3-butadiene (9) and 2,3-diphenyl-1,3-butadiene (10) and can be used in reactions with suitable dienophiles followed by aromatization to prepare areno-bridged [3.2]paracyclophanes. Similarly, 10,11-diethylidene[3.2]paracyclophane (7) was obtained from 10,11-diethyl[3.2]paracyclophane-10-ene (6) and reacted with dimethyl acetylenedicarboxylate.
DA  - 1989
DO  - 10.1002/cber.19891221216
KW  - [3.2]Paracyclophane-10-ene
KW  - Diels-Alder reaction
KW  - Cyclophanes
KW  - benzo-bridged
LA  - ger
IS  - 12
M2  - 2299
PY  - 1989
SN  - 0009-2940
SP  - 2299-2302
T2  - Chemische Berichte
TI  - 10,11-Dimethylen[3.2]paracyclophan: ein Cyclophanobutadien als Synthesebaustein für Benzo-verbrückte [3.2]Paracyclophane
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-17835063
Y2  - 2024-11-21T13:17:35
ER  -