Pyrolysis of 1-alkylazetidinone derivatives: A versatile route toward electron-rich alkenes, C-1 allylation and/or homologation of aldehydes

Autor:	Nouria A. Al-Awadi, Osama M. Habib, Yehia A. Ibrahim
Rok vydání:	2017
Předmět:	High energy 010405 organic chemistry Chemistry 010402 general chemistry 01 natural sciences Cycloaddition 0104 chemical sciences Analytical Chemistry Fuel Technology Yield (chemistry) Reagent Organic chemistry Stereoselectivity Staudinger reaction Pyrolysis
Zdroj:	Journal of Analytical and Applied Pyrolysis. 125:162-168
ISSN:	0165-2370
DOI:	10.1016/j.jaap.2017.03.023
Popis:	1-Alkyl-3-phenoxy- β -lactams have been synthesized by the standard Staudinger ketene-imine [2+2] cycloaddition. The corresponding β -thiolactams have readily been obtained in good yields by thiation with Lawesson's reagent. Static pyrolysis (STP) as well as FVP of these β -lactams and β -thiolactams led essentially to stereoselective synthesis of Z -alkenes. The 3-allyloxy-1-alkyl- β -lactams and β -thiolactams have also been prepared and gave upon pyrolysis 4-pentenal derivatives. Pyrolysis of 1-alkyl- β -lactams offers better yield than those reported from the corresponding 1-aryl derivatives, it also provides an easy access to the high energy electron-rich Z -alkenes and the synthetically important 4-pentenal.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d6e714984a8652ee68fc9be3593b77e6 https://doi.org/10.1016/j.jaap.2017.03.023 Zobrazit plný text záznamu Full Text from ScienceDirect