Premium
Photoenolization of 4‐Naphthoyl[2.2]paracyclophanes
Author(s) -
Hopf Henning,
Laue Thomas,
Zander Maximilian
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270527
Subject(s) - chemistry , context (archaeology) , enol , hydrogen , medicinal chemistry , photochemistry , proton , bridge (graph theory) , stereochemistry , organic chemistry , catalysis , medicine , paleontology , physics , quantum mechanics , biology
When ethanolic solutions of 4‐(1‐naphthoyl)[2.2]paracyclophane (3) and 4‐(2‐naphthoyl)[2.2]paracyclophane (4) are subjected to UV irradiation at low temperature, 1,5‐hydrogen migration of the 2‐H bridge proton to the carbonyl group takes place, leading to the enol of type 2. In the context of mechanistic considerations the triplet spectroscopic properties of 3 and 4 are discussed.