Helvetica Chimica Acta p. 1734 - 1747 (1984)
Update date:2022-08-03
Topics:
Scheller, Markus E.
Frei, Bruno
The syntheses and the photolyses of the acylsilane 1 and the corresponding methyl ketone 2 are described.On n,?*-excitation, the silyl ketone 1 as well as the methyl ketone 2 undergo a Norrish type II reaction involving γ-H-abstraction and fragmentation to the diene 12, and acetone (20) or the acylsilane 26, respectively.The methyl ketone 2, but not the acylsilane 1, isomerizes to cyclobutanols (21A-D).Additionally, compound 1 shows photochemical behavior typical of acylsilanes undergoing rearrangement to the siloxycarbene intermediate c.Insertion of c into the O-H-bond of the enol 28 leads to compound 13.Initial trapping of the siloxycarbene c by H2O, however, gives rise to the formation of compounds 16-18.As minor photolysis products of 1, the isomers 14 and (Z)-15 were formed; however, on vapor phase thermolysis (520o) of 1, compounds 14 and (E/Z)-15 were obtained in 92percent combined yield.To a small extent the acylsilane 1 also undergoes Norrish type I cleavage leading to the acid 19.
View MoreTianjin Hedong Red Cliff Chemical Reagent Factory
Contact:+86-022-84780548
Address:Li Ming Zhuang Gong Ye Yuan,Dongli District,Tianjin,China
Contact:+86-0760-85282375
Address:zhongjing road,zhongshan torch hi-tech industrial development zone
Changzhou Ruiping Chemical Co., Ltd
website:http://www.wishchem.com
Contact:+86-519-82324280
Address:No.288-1 Huacheng Road, Jintan
Laohekou huacheng Trade Co., Ltd.
Contact:+86-710-8360685
Address:No. 85, Beijing Road, Laohekou City, Hubei Province, China
Yangling Ciyuan biotech Co., Ltd.
Contact:86-15802970736
Address:2-1804, International Park Mansion, No.2, South Fengdeng Road, Lianhu District
Doi:10.1016/j.bioorg.2019.102930
(2019)Doi:10.1055/s-2007-983783
(2007)Doi:10.1021/jm00383a023
(1985)Doi:10.1016/j.jorganchem.2007.05.016
(2007)Doi:10.1007/BF00505963
(1984)Doi:10.1021/ja01153a082
(1951)