4949-20-6Relevant articles and documents
Diels-Alder adducts of of ortho-benzoquinones: Rearrangements and further transformations
Carlini, Rina,Higgs, Kerianne,Taylor, Nicholas,Rodrigo, Russell
, p. 805 - 816 (1997)
ortho-Benzoquinones substituted with an electron-withdrawing group (EWG = CO2Me, COSMe, COCH3, CHO) at C-3 or C-4 react as dienophiles at the C3 - C4 double bond in Diels-Alder reactions with several dienes, with predictable regiochemistry. The adducts undergo migration of the "angular" EWG substituent with concomitant aromatization to produce substituted catechols. The bicyclic products can be oxidized in situ and annelated by a further Diels-Alder reaction to yield 9,10-phenanthraquinone systems. When (2E)-2,4-pentadienol is employed as the diene in the second cycloaddition, reaction of the alcoholic hydroxyl group with one of the quinone carbonyl groups results in the production of tetracyclic lactols 22a, 22b, and 23.
Palladium-Promoted Neutral 1,4-Brook Rearrangement/Intramolecular Allylic Cyclization Cascade Reaction: A Strategy for the Construction of Vinyl Cyclobutanols
Zhang, Hao,Ma, Shiqiang,Yuan, Ziyun,Chen, Peng,Xie, Xingang,Wang, Xiaolei,She, Xuegong
supporting information, p. 3478 - 3481 (2017/07/15)
A cascade reaction to build vinyl cyclobutanol rings through activation of vinyl epoxides by palladium, followed by 1,4-Brook rearrangement and intramolecular cyclization with a palladium complex of the resulting carbon anion, is described. Through this cascade reaction, several highly substituted cyclobutanol substrates were achieved in good yields with high stereoselectivities.
Production of renewable 1,3-pentadiene from xylitol via formic acid-mediated deoxydehydration and palladium-catalyzed deoxygenation reactions
Sun, Ruiyan,Zheng, Mingyuan,Li, Xinsheng,Pang, Jifeng,Wang, Aiqin,Wang, Xiaodong,Zhang, Tao
supporting information, p. 638 - 642 (2017/02/26)
A two-step synthetic approach for the production of renewable 1,3-pentadiene was reported: xylitol deoxydehydration (DODH) by formic acid to 2,4-pentadien-1-ol, 1-formate (2E), followed by deoxygenation to 1,3-pentadiene over Pd/C. The overall carbon yield of 1,3-pentadiene reached 51.8% under the optimized conditions.