TY - JOUR
T1 - Formation of diethyl 2-amino-1-cyclopentenylphosphonates
T2 - A simple synthesis with a unique mechanism
AU - Al Quntar, Abed Al Aziz
AU - Srivastava, Hemant Kumar
AU - Srebnik, Morris
AU - Melman, Artem
AU - Ta-Shma, Rachel
AU - Shurki, Avital
PY - 2007/6/22
Y1 - 2007/6/22
N2 - (Chemical Equation Presented) Reaction of diethyl 5-chloro-1- pentynylphosphonate with primary and secondary amines produces novel 2-amino-1-cyclopentenylphosphonat.es, 1, in excellent isolated yields (79-88%). Calculations supported by experimental facts point to a two-step mechanism: an initial amine addition to give a zwitterionic intermediate followed by cyclization and proton transfer. Calculations rule out the formation of an enamine as an intermediate.
AB - (Chemical Equation Presented) Reaction of diethyl 5-chloro-1- pentynylphosphonate with primary and secondary amines produces novel 2-amino-1-cyclopentenylphosphonat.es, 1, in excellent isolated yields (79-88%). Calculations supported by experimental facts point to a two-step mechanism: an initial amine addition to give a zwitterionic intermediate followed by cyclization and proton transfer. Calculations rule out the formation of an enamine as an intermediate.
UR - https://www.scopus.com/pages/publications/84961978627
U2 - 10.1021/jo070535b
DO - 10.1021/jo070535b
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C2 - 17523670
AN - SCOPUS:84961978627
SN - 0022-3263
VL - 72
SP - 4932
EP - 4935
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -