1992 Fiscal Year Final Research Report Summary
PREPARATION OF OLEFINS AND SMALL RING COMPOUNDS BY THE USE OF 2-SELENOAZAAROMATIC COMPOUNDS
| Project/Area Number |
03640462
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | AOYAMA GAKUIN UNIVERSITY |
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Principal Investigator |
OYO Mitsunobu AOYAMA GAKUIN UNIVERSITY, COLLEGE OF SCIENCE AND ENGINEERING PROFESSOR OF CHEMISTRY, 理工学部, 教授 (90082792)
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| Project Period (FY) |
1991 – 1992
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| Keywords | Organoselenium Compound / Olefin / Selenetane / Stereospecific Reaction |
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| Research Abstract |
1) Reaction of 2-(2-oxoalkylseleno)benzazoles 1(X = S, O, N-Me) with allylic Grignard reagents in the presence of BF_3・OEt_2 afforded the corresponding selenoalcohols 2(X = S, O, N-Me ; R^2 = H or Me)which were converted into 1,4-dienes 3 by treatment with bases.
2) The hydride reduction of selenoketones1(X = S,O)gave selenoalcohols4. Benzoxazole derivatives were found to afford syn-selenoalcohols(syn-4) in preference to anti-isomers, While reverse was found for benzthiazole derivatives. On treatment with base, anti-selenoalcohols(anti-4)and syn-selenoalcohols(syn-4)respectively gave E-olefins(E-5)and Z-olefins(Z-5).
3)The reaction of 2-(benzoylalkylseleno)azole 1(X = S or O ; R = R^1 = Ph)with alcohols(R^2OH)in the presence of tributylphosphine gave 2-alkylseleno-azoles 6 in moderate to good yields.
4) When 2-(3-hydroxyalkylseleno)benzoxazoles 7 were treated with KH, selenetanes 8 or spiro compounds 9, the precursor of selenetane, were isolated, depending on the reaction conditions.
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