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Acta Chimica Sinica ›› 1991, Vol. 49 ›› Issue (2): 205-208. Previous Articles
Original Articles
江致勤;王延
发布日期:
JIANG ZHIQIN;WANG YAN
Published:
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Me gibberellate (I) undergoes sensitized photooxidn. in solution, leading to the formation of ene-reaction products, 15-enol II (R = CH2OH) and 15-enal II (R = CHO). Among sensitizers, 9, 10-dicyanoanthracene (DCA) and lumiflavin (LF) show higher reactivities on the reaction. A singlet oxygen mechanism is proposed based on several evidences. The reaction exhibits high chemoselectivity, i.e. the title reaction occurs exclusively at 16-exo double bond but no reaction at the ring double bond. This is rationalized in terms of ring-strain enhanced reactivity of the exo double bond towards electrophilic 1O2 as well as the neighboring group participation of 13-hydroxy on the exo double bond.
Key words: GIBBERELLIC ACID, SINGLET OXYGEN, PHOTOSENSITIZATION OXIDATION, METHYL ESTER P
CLC Number:
O644
JIANG ZHIQIN;WANG YAN. Studies on photooxidation[J]. Acta Chimica Sinica, 1991, 49(2): 205-208.
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