Alkylations of isoquinoline via lithium aluminium hydride.
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| Other Authors: | , , |
| Format: | Thesis Book |
| Language: | English |
| Published: |
1983.
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| Subjects: | |
| Online Access: | Link to ProQuest Copy Link to OAKTrust copy |
| Abstract: | Lithium aluminium hydride (LAH) in tetrahydrofuran (THF) reacted rapidly with isoquinoline to give lithium tetrakis dihydroisoquinoline aluminate (LTDA). Proton and ('13)C NMR spectra indicated the presence of only 1,2- but not 1,4-dihydro isomer. Unlike isoquinoline, pyridine or quinoline was less reactive and gave the corresponding 1,2- as well as 1,4-dihydro ligands. In THF, the isoquinoline-LAH intermediate (LTDA) reacted with methyl iodide, ethyl bromide, n-propyl bromide, allyl bromide, n-butyl bromide and benzyl chloride but not sec- and tert-butyl bromides to give the corresponding 4-substituted isoquinolines. In diethyl ether (Et(,2)O), all of these alkyl halides reacted. The yields of products ranged from 25 to 64% in THF, and 43 to 61% in Et(,2)O. For most reactions, yields of alkylated products were substantially higher in Et(,2)O than in THF: a one-electron transfer mechanism was proposed. ('1)H NMR and mass spectra for the 4-substituted isoquinolines were reported. These reactions also gave other minor products including 1,2,3,4-tetrahydroisoquinoline, monoalkylated tetrahydroisoquinolines and dialkylated tetrahydroisoquinolines. |
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| Item Description: | "Major subject: Chemistry." Typescript (photocopy). Vita. |
| Physical Description: | xii, 178 leaves : illustrations ; 29 cm |
| Bibliography: | Includes bibliographical references (leaves 110-115). |