2001 Fiscal Year Final Research Report Summary
Synthesis and solid state Chemistry of push-pull type substituted allene derivatives
| Project/Area Number |
11640543
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Kitasato University |
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Principal Investigator |
MAZAKI Yasuhiro Kitasato University, School of Science, Associate Professor, 理学部, 助教授 (60199677)
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| Project Period (FY) |
1999 – 2000
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| Keywords | allene derivatives / synthesis / push-pull type substitution / solid state chemistry / 固体化学 |
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| Research Abstract |
1-(4N,N-Dimethylaminophenyl)-3-(4-nitrophenyl)-1,3-diphenylallene 1 (pale yellow liquid) and 1-(4-carbomethoxyphenyl)-3-(4-N,N-dimethylarrunophenyl)-1,3- diphenylallene 2 (colorless solid) have been synthesized as push-pull type substituted allene derivatives and examined their properties caused by push-pull type polarization. 1-(4-N,N-dimethylaminophenyl)-1,3,3-triphenyl-allene 3, 1-(4-nitrophenyl)-1,3,3-triphenylallene 4, 1-(4- carbomethoxyphenyl) -1,3,3- triphenylallene 5, tetraphenylallene 6 have been also synthesized as the reference compounds.
Although it is expected the reciprocally opposite polarization effects of both substituents (push and pull) raise the contribution of "carbene like" resonance structure in allene moiety, it has been suggested that the polarization through benzene rings was little effective to allene part by the comparison of X-ray molecular structures of reference compounds 3 and 6, 13C NMR chemical shifts and electronic spectra in these series.
X-ray crystallographic analysis of push-pull derivatives, examination of enclathration for 1 and 2, solid state photoreaction of 1, 2 were prevented by low stability and poor crystallinity of 1 and 2.
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