68797-94-4Relevant articles and documents
Synthesis of 23-, 25-, 27-, and 29-Membered (Z)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization
Iwasaki, Tomoya,Tajimi, Yuka,Kameda, Kenta,Kingwell, Callum,Wcislo, William,Osaka, Kazuyuki,Yamawaki, Mugen,Morita, Toshio,Yoshimi, Yasuharu
, p. 8019 - 8026 (2019/06/27)
A new strategy for the synthesis of 23-, 25-, 27-, and 29-membered (Z)-selective unsaturated and saturated macrocyclic lactones from commercially available 16- and 17-membered macrocyclic lactones and bromoalcohols by Wittig reaction, Yamaguchi macrolactonization, and photoinduced decarboxylative radical macrolactonization is described. The position of the unsaturated part in the macrocyclic lactones can be controlled by changing the number of carbons in the starting materials. This protocol can provide facile access to the desired large-ring (Z)-selective unsaturated and saturated macrocyclic lactones from simple starting materials.
Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage
Lu, Ping,Hou, Tianyuan,Gu, Xiangyong,Li, Pixu
supporting information, p. 1954 - 1957 (2015/04/27)
A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.
Primary alkyl bromides from dimethylthiocarbamates
Moynihan, Meghan F.,Tucker, Joseph W.,Abelt, Christopher J.
experimental part, p. 3565 - 3568 (2009/06/18)
The conversion of primary alkyl dimethylthiocarbamates into alkyl bromides using the Vilsmeier reagent occurs in high yields in the presence of other non-acid sensitive and non-nucleophilic functional groups. Georg Thieme Verlag Stuttgart · New York.