TY - JOUR
T1 - Photochemical Isomerization of Cyclohept-1-ene-1-carbaldehyde
T2 - Strain-Release Cycloadditions and Ene Reactions
AU - Schwinger, Daniel P.
AU - Pickl, Thomas
AU - Bach, Thorsten
N1 - Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society
PY - 2023/9/1
Y1 - 2023/9/1
N2 - Cyclohept-1-ene-1-carbaldehyde undergoes photoinduced E → Z isomerization at λ = 350 nm. The ring strain facilitates Diels-Alder cycloaddiions with 1,3-dienes, [3 + 2] cycloadditions with 1,3-dipoles, and ene reactions with olefins. Products are trans-fused at the cycloheptane core and were obtained in yields of up to 82%. Single crystal X-ray analyses corroborated the constitution and relative configuration of key products. With BF3 as a Lewis acid and 2,3-dimethylbuta-1,3-diene, cyclohept-1-ene-1-carbaldehyde reacted in the dark and rearranged stereoselectively to a tricyclic ketone (87%).
AB - Cyclohept-1-ene-1-carbaldehyde undergoes photoinduced E → Z isomerization at λ = 350 nm. The ring strain facilitates Diels-Alder cycloaddiions with 1,3-dienes, [3 + 2] cycloadditions with 1,3-dipoles, and ene reactions with olefins. Products are trans-fused at the cycloheptane core and were obtained in yields of up to 82%. Single crystal X-ray analyses corroborated the constitution and relative configuration of key products. With BF3 as a Lewis acid and 2,3-dimethylbuta-1,3-diene, cyclohept-1-ene-1-carbaldehyde reacted in the dark and rearranged stereoselectively to a tricyclic ketone (87%).
UR - http://www.scopus.com/inward/record.url?scp=85169167999&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c01311
DO - 10.1021/acs.joc.3c01311
M3 - Article
AN - SCOPUS:85169167999
SN - 0022-3263
VL - 88
SP - 12844
EP - 12852
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -