1966
DOI: 10.1016/s0040-4020(01)82142-6
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Organic mass spectrometry—V

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Cited by 36 publications
(10 citation statements)
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“…The position of molecular ion (M R ) corresponds to the sum of molecular masses of the substrates 1 i 2a (m/e ¼ 260), which in combination with the results of elemental analysis (CHN), allow us to assign the formula C 13 H 12 N 2 O 4 to the isolated cycloadducts. The fragmentation pattern of M R. is a combination of the fragmentation patterns characteristic of norbornenes [30][31][32] and nitrocycloalkanes, [33][34][35] but it does not allow differentiation between the stereoisomers. However, the stereochemistry assignment was possible with the aid of 1 H-NMR spectroscopy.…”
Section: Stereospecificity Of the Reaction Of Cyclopentadiene With E-mentioning
confidence: 99%
“…The position of molecular ion (M R ) corresponds to the sum of molecular masses of the substrates 1 i 2a (m/e ¼ 260), which in combination with the results of elemental analysis (CHN), allow us to assign the formula C 13 H 12 N 2 O 4 to the isolated cycloadducts. The fragmentation pattern of M R. is a combination of the fragmentation patterns characteristic of norbornenes [30][31][32] and nitrocycloalkanes, [33][34][35] but it does not allow differentiation between the stereoisomers. However, the stereochemistry assignment was possible with the aid of 1 H-NMR spectroscopy.…”
Section: Stereospecificity Of the Reaction Of Cyclopentadiene With E-mentioning
confidence: 99%
“…This was proposed by Goto et a1. 2 by analogy with the behavior of 5,6-d2 benzobicyclo (2.2.1) heptane and by Cristol et aL6 by analogy with the behavior of exo-dehydronorbornyl acetate; a direct experimental proof, using 5,6-d2 norbornene, has been provided by D~r s e y .~ The only other fragmentation of norbornene which has aroused interest is the loss of a methyl radical from the molecular ion. Biemann' suggested that this involved breaking the 1 , 7 (or 4, 7) bond followed by migration of a hydrogen atom from the 5 or 6 position to C-7; however, he was of the opinion that his hypothesis would not stand the test of a deuterium labeling experiment because of the possibility of hydrogen scrambling.…”
Section: Introductionmentioning
confidence: 97%
“…The 5-substituted 2-adamantanones are relatively stable under electron impact, except compound 8, and the compounds 1, 5, 6, 9 and 10 show the molecular ion a as a base peak. The fission of the molecular ion a is initiated by the familiar α-cleavage of ketones, which has been shown [18][19][20][21] to produce the most abundant fragments arising from the parent ion. In the present case, α-fission at the C2-C3 bond is attended, possibly in a concerted process, together with simultaneous hydrogen migration to C2, leading to the central intermediate b (Scheme 2).…”
Section: Resultsmentioning
confidence: 99%