Premium
Photochemisch induzierte Reaktionen von 3‐Amino‐2 H ‐azirinen
Author(s) -
Dietliker Kurt,
Heimgartner Heinz
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660126
Subject(s) - chemistry , regioselectivity , protonation , yield (engineering) , stereochemistry , cleavage (geology) , bond cleavage , ring (chemistry) , medicinal chemistry , mercury (programming language) , ion , catalysis , organic chemistry , materials science , geotechnical engineering , fracture (geology) , computer science , engineering , metallurgy , programming language
Photochemically Induced Reactions of 3‐Amino‐2 H‐azirines Irradiation of 3‐( N ‐methylanilino)‐2 H ‐azirines with a mercury low pressure lamp induces the cleavage of the C(2), C(3)‐ring bond thus affording nitrilio‐methanide dipols, substituted by an amino group at C(1). Depending on the substitution pattern at C(3), these intermediates can be trapped by dipolarophiles to yield five‐membered heterocycles with high regioselectivity, or they undergo a 1,4‐H‐shift forming 2‐azabutadiene derivatives. Further, the dipol is protonated at C(1) even by weak CH–acids.