%0 Journal Article
%A Wang, Kung K.
%A Shi, Chongsheng
%A Petersen, Jeffrey L.
%D 1998
%T A Facile Cascade Synthesis of 5,6-Diaryldibenzo[a,e]cyclooctenes
from (Z,Z)-1-Aryl-3,5-octadiene-1,7-diynes†
%U https://acs.figshare.com/articles/journal_contribution/A_Facile_Cascade_Synthesis_of_5_6-Diaryldibenzo_i_a_i_i_e_i_cyclooctenes_from_i_Z_i_i_Z_i_-1-Aryl-3_5-octadiene-1_7-diynes_sup_sup_/3710670
%R 10.1021/jo9802473.s002
%2 https://ndownloader.figshare.com/files/5801400
%K cyclooctenyl units
%K diastereomer
%K 1 H NMR spectrum
%K presence
%K dibenzo
%K Facile Cascade Synthesis
%K cyclooctene
%K cyclooctenyl units exhibits signals
%X Sequential treatment of (Z)-3-methyl-2-penten-4-ynal
(10) with the allenylborane 2 and
2-aminoethanol furnished 11. The use of 11 for
cross-coupling with aryl iodides followed by the
KH-induced
syn elimination of the coupled adducts 13 provided easy
access to a variety of dienediynes 14 for
subsequent conversions to
dibenzo[a,e]cyclooctenes
(sym-dibenzocyclooctatetraenes) 17. By
cross-coupling with 1,2- and 1,4-diiodobenzene, it was possible to obtain
19 and 25 having two dienediynyl
moieties. It was anticipated that the oligomers 21 and
26 containing multiple
dibenzo[a,e]cyclooctenyl units could thus be synthesized. The 1H NMR
spectrum of 32 having three
dibenzo[a,e]cyclooctenyl units indicates the presence of three diastereomers
32a−c in a random statistical
distribution of 2:1:1. Similarly, the 1H NMR spectrum
of 33 having two
dibenzo[a,e]cyclooctenyl
units exhibits signals that support the presence of two diastereomers
33a and 33b in a 1:1 ratio.
%I ACS Publications