TY - JOUR
T1 - Cycloaddition Reactions of Indenes. 3. 1:1 Adduct from 1,1-Dimethy 1-1 H-indene and Dimethyl Acetylenedicarboxylate
AU - Noland, Wayland E.
AU - Kameswaran, Venkataraman
PY - 1981/3
Y1 - 1981/3
N2 - In contrast to lH-indene (la) and 1-methyl-lH-indene (lb), which give stable 1:2 adducts (3a, 34%; 3b, 30%) and with la also a 1:3 adduct (4a; 40% from la; 71% from 3a) with dimethyl acetylenedicarboxylate (DMAD), 1,1-dimethyl-lfl-indene (Id) and DMAD gave as the only crystalline product a cycloadduct of different structural type, dimethyl la,7b-cts-dihydro-l,1-dimethyl-lfl-cyclopropa[o]naphthalene-2,3-dicarboxylate (5a, 14%), the structure of which has been confirmed by X-ray crystallography.
AB - In contrast to lH-indene (la) and 1-methyl-lH-indene (lb), which give stable 1:2 adducts (3a, 34%; 3b, 30%) and with la also a 1:3 adduct (4a; 40% from la; 71% from 3a) with dimethyl acetylenedicarboxylate (DMAD), 1,1-dimethyl-lfl-indene (Id) and DMAD gave as the only crystalline product a cycloadduct of different structural type, dimethyl la,7b-cts-dihydro-l,1-dimethyl-lfl-cyclopropa[o]naphthalene-2,3-dicarboxylate (5a, 14%), the structure of which has been confirmed by X-ray crystallography.
UR - http://www.scopus.com/inward/record.url?scp=2842514350&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=2842514350&partnerID=8YFLogxK
U2 - 10.1021/jo00320a017
DO - 10.1021/jo00320a017
M3 - Article
AN - SCOPUS:2842514350
SN - 0022-3263
VL - 46
SP - 1318
EP - 1322
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -