Abstract
The electron impact and collision-induced dissociation spectra of 2-(2-carbethoxy-1-imino-1-methylthio)-ethylene isoquinoline ylide (1), 2-(2-cyano-1-phenylamino-1-methylthio)-ethylene pyridine ylide (2), 2-(2-carboethoxy-1-amino-1-thio)-ethylene pyridine ylide (3), 2-(2-carboethoxy-1-amino-1-thio)-ethylene isoquinoline ylide (4) and 2-(1-N-phenylamide-1-cyano)-ethylene pyridine ylide (5) were studied. The molecular ions of compounds 1–4 were shown to undergo cyclization to the corresponding heterocyclic compounds, analogous to the reaction of compound 1 in solution. Proposed fragmentation schemes are presented based on tandem mass spectrometry and high resolution mass spectrometry data.
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References
1.
Zeller
P.
Meier
H.
and
Muller
E.
, Tetrahedron 28 , 5831 (1972 ).
2.
Meier
H.
and
Zeller
K.P.
, Angew. Chem. 87 , 52 (1975 ).
3.
Grützmacher
H.-F.
, Org. Mass Spectrom. 28 , 1375 (1993 ).
4.
Lebedev
A.T.
, Mass Spectrom. Rev. 10 , 91 (1991 ).
5.
Lebedev
A.T.
Alexeeva
T.N.
Kutateledze
T.G.
Mochalov
S.S.
Shabarov
Yu.S.
and
Petrosyan
V.S.
, Org. Mass Spectrom. 24 , 149 (1989 ).
6.
Lebedev
A.T.
Samguina
T.Yu.
Petrosyan
V.S.
Blumental
T.
Sipyaguin
A.M.
and
Kartsev
V.G.
, Org. Mass Spectrom. 27 , 730 (1992 ).
7.
Lebedev
A.T.
Kazaryan
A.G.
Sharbatyan
P.A.
Sipyagin
A.M.
Kartsev
V.G.
and
Petrosyan
V.S.
, Zh. Org. Khim. 24 (7 ), 1393 (1988 ).
8.
Glish
G.L.
and
Cooks
R.G.
J. Am. Chem. Soc. 100 (21 ), 6720 (1978 ).
9.
Bowie
J.H.
, Org. Mass Spectrom. 28 , 1407 (1993 ).
10.
Lebedev
A.T.
Bakoulev
V.A.
Hayes
R.N.
and
Bowie
J.H.
, Rapid Commun. Mass Spectrom. 5 , 234 (1991 ).
11.
Berseneva
V.S.
Bakoulev
V.A.
Mokrushin
V.S.
and
Lebedev
A.T.
, Khim. Geterotsikl. Soedin. 12 , 1639 (1989 ).
12.
Taylor
E.C.
and
Turchi
I.J.
, Chem. Rev. 79 , 181 (1979 ).