627-18-9Relevant articles and documents
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Nystrom
, p. 610 (1959)
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Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
Lambert, Tristan H.,Steiniger, Keri A.
supporting information, p. 8013 - 8017 (2021/10/25)
The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.
Acid-Catalyzed Intramolecular Ring-Opening Reactions of Cyclopropanated Oxabenzonorbornadienes with Carboxylic Acid Nucleophiles
Carlson, Emily,Ho, Angel,Koh, Samuel,Macleod, Matthew P.,Pounder, Austin,Tam, William
, (2021/12/02)
The present work demonstrates the ability of carboxylic acid tethered cyclopropanated oxabenzonorbornadienes (CPOBDs) to undergo ring-opening reactions in mild acidic conditions. The optimized reaction conditions involve the use of pTsOH in DCE at 90 °C. Two regioisomers are formed but the reactions are highly regioselective towards type 3 ring-opened products. It was observed that substitution at the C5 and aryl positions of CPOBD significantly hinders the ring-opening reactions leading to decreased yields of ring-opened products, although high regioselectivity for the Type 3 ring-opened products is still maintained. Herein, the first examples of acid-catalyzed intramolecular ring-opening reactions of CPOBD with carboxylic acid nucleophiles are reported.
Preparation of useful building blocks, α-iodo- and bromoalkanols from cyclic ethers using the Dowex H+/NaX (X = I, Br) approach
Turhanen, Petri A.,Veps?l?inen, Jouko J.
, p. 15937 - 15940 (2016/02/19)
Our recently reported novel green chemistry tool was effectively used for opening cyclic ethers to produce α-iodo- and bromoalkanols. The synthesis of 4-iodobutanoic acid from γ-butyrolactone has also been described. The method is based on the use of a dried Dowex H+/NaX (X = Br, I)-system, which is effective at producing α-iodoalkanols and some α-bromoalkanols from commercially available cyclic ethers. Additionally, opening of three different crown ethers to form α-iodo(polyethylene)glycols with various chain lengths is demonstrated. Haloalkanols are important building blocks in synthetic chemistry e.g. for medicinal chemistry purposes.