By Guenter Grethe
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Extra resources for Isoquinolines, Part 1 (The Chemistry of Heterocyclic Compounds, Volume 38)
The dominant feature is the loss of a substituent from C-1 (or C-3) to form an iminium cation that is usually the base peak. Thus the 1-isobutyl derivative s h ~ w s ' 'a~weak M' (78),and the base peak corresponds to the ion 79. l-Benzyl-1,2,3,4tetrahydroisoquinoline derivatives occur abundantly, often with oxygen Me0 Me Me mle 176 79 78 1+’ Me0 HO 80 bl mle 192 (4%) Q Me0 A E HO N ’ m / e 178 (23%) OMe OMe %heme 4 26 ’ +Q OMe 111. Spectroscopic Properties 7-7 functions on both the benzyl and isoquinoline benzenoid rings.
Spectroscopic Properties 21 obtained (54: R = H. M2 = 68 and 54; R = Me, M,= 70) compare with t h e values of 73 and 75, respectively derived from esr measurements. 'H 54 E. Mass Spectrometry The mass spectrum of isoquinoline exhibits"" a stable molecular ion followed initially by a loss of HCN (55-56); I3C studies have not been m/e 129 m/e 102 55 56 m/e 76 undertaken to determine whether C-1 or C-3 is preferentially lost. A methyl substituent, especially at C-1 or C-3, reduces the importance of this process'03 and introduces a new mode of fragmentation through the formation of an azatropylium ion such as 57 (Eq.
When l-methyl-3,4-dihydroisoquinoline is photolyzed in the meso and racemic forms of 174 are formed. 275 XOR -M 51 IV. Reactions Me0 OMe OMe 167 168 R = H o r Me Me0 OH O 'N $,M e 0 169 170 172 171 174 173 ( c ) Oxidation 1,2,3,4-TetrahydroisoquinoIinesmay be converted into 3,3-dihydroisoquinolines or into the fully aromatic derivatives by catalytic or chemical methods. ' Although catalytic dehydrogenation is widely used, (i) CATALYTIC. the conditions are often severe, and failures or poor yields have been 52 Properties and Reactions of Isoquinolines reported.
Isoquinolines, Part 1 (The Chemistry of Heterocyclic Compounds, Volume 38) by Guenter Grethe