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제107회 대한화학회 학술발표회, 총회 및 기기전시회 안내 1,3-Dipolar Cycloaddition Reactions of meso-Alkylidene Porphyrins

등록일
2011년 2월 9일 10시 33분 16초
접수번호
0101
발표코드
Ⅱ-ORGN.P-219 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
목 <발표Ⅱ>
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
이창희, 박도우
강원대학교 화학과, Korea
1,3-Dipolar cycloaddition reaction is increasingly popular in the field of the chemical modification of porphyrin skeleton. We applied this reaction to the chemical transformation of meso-alkylidene porphyrins that we have synthesized recently. The reaction of in situ generated azomethine ylide (generated from the reaction of N-methyl glycine with formaldehyde) with diethyl malonylidene-(m-benzi)thiaporphyrin or its expanded analogs afforded cyclized adducts. The reaction took place regioselectively on the pyrrole adjacent to the meso-alkylidenyl double bond. Other regioisomers were also formed as minor products. All the products were identified by spectroscopic means and MOLDI-TOF mass spectrometry. The regioselectivity can be interpreted by the fact that the dipolarophile (porphyrin) must be electron deficient (lower LUMO) for fast reaction. The reaction can be applied to the construction of reduced porphyrins which are usful in various porphyrin-related applications.

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