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Impact of peripheral substituents in regioselective synthesis of position-10 or position-20 bromo-bacteriochlorins

Title
Impact of peripheral substituents in regioselective synthesis of position-10 or position-20 bromo-bacteriochlorins
Authors
Dukh, MykhayloJoshi, PennyOhkubo, KeiTabaczynski, WalterPatel, Nayan J.Missert, Joseph R.Zador, SteveFukuzumi, ShunichiPandey, Ravindra K.
Ewha Authors
Shunichi Fukuzumi
SCOPUS Author ID
Shunichi Fukuzumiscopus
Issue Date
2017
Journal Title
TETRAHEDRON LETTERS
ISSN
0040-4039JCR Link
Citation
vol. 58, no. 9, pp. 851 - 854
Keywords
ChlorinBacteriochlorinBovine serum albuminDensity functional calculations
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Bacteriochlorins derived either from chlorophyll-a or bacteriochlorophyll-a on reacting with pyridinium bromide or N-bromosuccinimide (NBS) gave the corresponding 10- or 20-bromo analogues. In contrast to methyl bacteriopyropheophorbide-a, which afforded 10-bromo derivative, the 7-keto and 8-ketobacterichlorins under similar reaction conditions gave the corresponding 20-bromo analogues exclusively. In both series, the nature of substituents present at position-3 did not make any difference in the reaction outcome. Density functional calculations were carried out to clarify the difference in reactions outcome. Density functional calculations were carried out to clarify the difference in reactivity of bromination at 10- and 20- mesa positions. (C)2017 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.tetlet.2017.01.044
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자연과학대학 > 화학·나노과학전공 > Journal papers
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