COMPARISON OF PHOTOCHEMICAL REACTIONS OF AROMATIC CARBONYL COMPOUNDS WITH A SILYL KETENE THIOACETAL AND A SILYL KETENE ACETAL

Title
COMPARISON OF PHOTOCHEMICAL REACTIONS OF AROMATIC CARBONYL COMPOUNDS WITH A SILYL KETENE THIOACETAL AND A SILYL KETENE ACETAL
Author(s)
조대원문경민임숙현김성홍[김성홍]이인옥[이인옥]윤웅찬[윤웅찬]Patrick S. Mariano[Patrick S. Mariano]
Keywords
SINGLE-ELECTRON TRANSFER; PHOTOADDITION REACTIONS; ELECTROCHEMICAL OXIDATION; STEREOSELECTIVE-SYNTHESIS; ORGANOSILICON COMPOUNDS; MICHAEL REACTIONS; ACID-CHLORIDES; ALLYLSILANES; ALDOL; CYCLIZATION
Issue Date
201501
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
HETEROCYCLES, v.90, no.2, pp.978 - 988
Abstract
Photoaddition reactions of carbonyl compounds with silyl ketene thioacetals have been explored and the results are compared to those arising from investigations of analogus reactions with silyl ketene acetals. Observations made in this study show that photoirradiation of benzaldehyde (8) and benzophenone (9) and with the dimethyl substituted silyl ketene thioacetal (13) promotes reactions that take place predominantly via Paterno-Buchi type [2+2]-cycloaddition pathways to produce oxetanes. In addition, photoreactions between acetophenone (10) and p-cyanoacetophenone (11) and 13 occur via competitive sequential single electron transfer (SET)-desilylation or [2+2]-cycloaddition modes. Lastly, photochemical reaction of the highly electron deficient carbonyl compound, p-trifiuoromethylacetophenone (12), and 13 gives rise to exclusive formation of beta-hydroxythioester arising via the SET pathway. In contrast, photochemical reactions of all of these aromatic carbonyl compounds with the analogous dimethyl substituted silyl ketene acetal 14 take place predominantly via a sequential SET-desilylation pathway to form beta-hydroxyesters. A comparison of these results reveals that replacement of an alkoxy by alkylthio group in the ketene derivatives brings about dramatic changes in chemoselectivities of the photoreactions with aryl-substituted ketones.
URI
http://hdl.handle.net/YU.REPOSITORY/33725http://dx.doi.org/10.3987/COM-14-S(K)69
ISSN
0385-5414
Appears in Collections:
이과대학 > 화학생화학부 > Articles
문과대학 > 중국언어문화학과 > Articles
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