TY - JOUR
T1 - Unusual photorearrangements of homoconjugated diacylcyclohexa-2,4-dienes
AU - Oren, Jakob
AU - Schleifer, Leah
AU - Weinman, Sarah
AU - Fuchs, Benzion
PY - 1988
Y1 - 1988
N2 - The unprecedented triplet sensitized electrocyclic ring opening of various 3a,7a-diacyl-3a,7a-dihydroindans (3)-(5) to the corresponding cyclononatriene derivatives (7)-(11) is reported, direct irradiation at all absorbing wavelengths of the keto-ester (5) resulting in a diastereoselective oxa-di-π-methane (ODPM) rearrangement to the tricyclic product (6); dimethyl 1,2-dimethyl-1,2-dihydrophthalate (15) reacted similarly to give dimethyl E,E,E-2,7-dimethyl-2,4,6-octatrienoate (16), whose structure has been determined by single crystal X-ray diffraction analysis.
AB - The unprecedented triplet sensitized electrocyclic ring opening of various 3a,7a-diacyl-3a,7a-dihydroindans (3)-(5) to the corresponding cyclononatriene derivatives (7)-(11) is reported, direct irradiation at all absorbing wavelengths of the keto-ester (5) resulting in a diastereoselective oxa-di-π-methane (ODPM) rearrangement to the tricyclic product (6); dimethyl 1,2-dimethyl-1,2-dihydrophthalate (15) reacted similarly to give dimethyl E,E,E-2,7-dimethyl-2,4,6-octatrienoate (16), whose structure has been determined by single crystal X-ray diffraction analysis.
UR - http://www.scopus.com/inward/record.url?scp=37049084377&partnerID=8YFLogxK
U2 - 10.1039/C39880000315
DO - 10.1039/C39880000315
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AN - SCOPUS:37049084377
SN - 0022-4936
SP - 315
EP - 317
JO - Chemical Communications
JF - Chemical Communications
IS - 4
ER -