1992 Fiscal Year Final Research Report Summary
Selective Hydrogenation of Cyclic alpha,beta-unsaturated ketones containing sulfur atom with the Wilkinson type Catalyst.
| Project/Area Number |
03640434
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
有機化学一般
|
|---|
| Research Institution | Miyagi University of Education |
|---|
Principal Investigator |
HANAYA Kaoru Miygi University of Education, Faculty of Education, Professor, 教育学部, 教授 (40006937)
|
|---|
| Project Period (FY) |
1991 – 1992
|
| Keywords | Wilkinson catalyst / Homogeneous hydrogenation / 4-Thiochromone / 4-Thiochromanone / Selective hydrogenation |
|---|
| Research Abstract |
The hydrogenation of 4-thiochromones [1], 3-benzyliden-4-thiochromanones [2] and these 1,1-dioxides [3], [4] by the Wilkinson rhodium catalyst was examined and was obtained the results as follows.
1.Wilkinson catalyst is inactive for [1] and starting material was recovered nearly quantitatively except 2-methy1-4-chromone which hydrogenated to corresponding thiochromanone in Ca. 30% yield.
2.The hydrogenation of 2,3-dimethy1-4-thiochromone gave the 1:1 mixture of cis- and trans-2,3-dimethy1-4-chromanone.
3.The hydrogenation [3] and [4] gave the corresponding 4-thio-chromanone 1,1-dioxide in a high yield, respectively.
4.The hydrogenation [2] gave the corresponding 3-benzy1-4-thio-chromanone (30-40%) along with the isomerized product (3-benzy1-4-thiochromone, 10-15%).
From these results, the behavioral difference of [1] and [2], [1] and [3] in the hydrogenation with Wilkinson catalyst and a mechanism of the hydrogenation with Wilkinson catalyst was discussed.
|
