50407-04-0Relevant articles and documents
Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates
Banerjee, Amit,Hattori, Tomohiro,Yamamoto, Hisashi
, (2021/06/16)
Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).
One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides
Suleymanov, Abdusalom A.,Scopelliti, Rosario,Fadaei Tirani, Farzaneh,Severin, Kay
supporting information, p. 3323 - 3326 (2018/06/11)
A simple and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure is based on the reaction of Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable the regioselective formation of triazenes via an intramolecular cyclization step. The new method can be used for the preparation of aryl, heteroaryl, vinyl, and alkyl triazenes. The synthetic utility of vinyl triazenes is demonstrated by acid-induced C-N, C-O, C-F, C-P, and C-S bond-forming reactions.
Synthesis of Perhydro-1,3-diazine-2-thiones from β-Chloro Imines
Sulmon, Paul,Kimpe, Norbert De,Schamp, Niceas,Declercq, Jean-Paul
, p. 2587 - 2590 (2007/10/02)
The reaction of β-chloro imines with methanol gave rise to β-alkylamino acetals via intermediate 2-methoxyazetidines.If an aromatic β-chloro imine was used under these conditions, 1-methoxy-2-methyl-1-phenyl-1-propene was also formed.The reaction of β-chloro imines with potassium thiocyanate in methanol gave rise to perhydro-1,3-diazine-2-thiones in 10-55percent yield in addition to β-alkylamino acetals, again via methoxyazetidines.