Development of New Photochemical Reactions of Phenols Promoted by Lewis Acid and its Synthetic Application
| Project/Area Number |
03805077
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
Synthetic chemistry
|
|---|
| Research Institution | Osaka University |
|---|
Principal Investigator |
TOBE Yoshito Osaka University, Faculty of Engineering Science, Associate Professor, 基礎工学部, 助教授 (60127264)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
KAKIUCHI Kiyomi Osaka University, Faculty of Engineering, Research Assistant, 工学部, 助手 (60152592)
|
|---|
| Project Period (FY) |
1991 – 1992
|
| Project Status |
Completed (Fiscal Year 1992)
|
| Budget Amount *help |
¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1992: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1991: ¥1,200,000 (Direct Cost: ¥1,200,000)
|
|---|
| Keywords | Phenol / Lewis Acid / Photochemical Reaction / Isomerization Reaction / Addition Reaction / フェノ-ル |
|---|
| Research Abstract |
We have found new photochemical reactions of phenol derivatives promoted by Lewis acid and have developed new method for carbocyclic ring construction starting from readily available aromatic compounds.
1. We found that irradiation of 3-methoxyphenol (1) in the presence of aluminum bromide gave 4-methoxybicyclo [3.1.0] hexenone (2) in a good yield.
2. We found that irradiation of 1-naphthol (3) in the presence of aluminum halides afforded ringcontracted halomethylindanone (4) in a good yield. indanone 4 was converted to the cyclopropane-containing compound 5 quantitatively by treatment with a base.
3. We have already reported that 2-naphthol (6) produced the [2+2] cycloadduct with ethylene by irradiation in the presence of Lewis acid. In order to clarify the mechanism of this novel reaction, we investigated the effect of olefins and Lewis acids in this reaction.
4. We found that the reactivity of 1-naphthol (3) and its derivatives was divergent and it was critically dependent on the position of the substituent. Thus 3 and its 3-methyl derivative gave [2+2] cycloadducts 7 in good yields. On the other hand, 2-alkyl and 6-methoxy derivatives yielded ringcontracted adducts 8 having an indenone core as the major products.
|
Report
(3 results)
Research Products
(12 results)
