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Type II photoreaction of benzoyl‐ and (benzoylmethyl)cyclohexanones: cyclohexanone ring inversion and other factors determining their photoreactivities by Tadashi Hasegawa; Yiming Yang; Shuichi Kikuchi; Takayuki Nakamura; Yutaka Maeda is a Chemistry article available to read on EtoBox.
What is Type II photoreaction of benzoyl‐ and (benzoylmethyl)cyclohexanones: cyclohexanone ring inversion and other factors determining their photoreactivities about?
## Abstract X‐ray crystallographic structure analysis showed that a molecule of 2‐benzoylcyclohexanone (**2**), which undergoes an efficient Type II reaction in solution but not in the crystalline state, is in a keto and chair form with an equatorial benzoyl group. Irradiation of 3‐benzoylcyclohexanone (**3**) gives 7‐phenylhepten‐4,7‐dione (**4**, 61%) and a mixture of cyclization products **5** (25%). High photoreactivity of **2** and **3** is caused by the efficient cyclohexanone ring inversion. Upon irradiation, 2‐(benzoylmethyl)cyclohexanone (**6**) gives acetophenone (**7**), 2‐cyclohexenone (**8**) and the cyclobutanol **9** in 59, 59 and 35% yield, respectively, and 1‐phenyl‐3‐propylpentan‐1,4‐dione (**10**) gives **7** and the cyclobutanol **11** in 73 and 4% yield, respectively. The quantum yields for the disappearance of **6** and **10** are 0.68 and 0.67, respectively. Irradiation of 2‐(benzoylmethyl)‐2‐ethoxycarbonylcyclohexanone (**12**) gives **7** and the cyclobutanol **13** in 46 and 51% yield, respectively. The quantum yield for the disappearance of **12** is 1.00, so that reverse hydrogen transfer is suppressed by intramolecular hydrogen bonding in the 1,4‐biradi
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- Author
- Tadashi Hasegawa; Yiming Yang; Shuichi Kikuchi; Takayuki Nakamura; Yutaka Maeda
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0894-3230)
- Published
- 2005
- Field
- Chemistry (Physical Sciences)