The Chromyl Chloride Oxidation of α-Pinene
The oxidation of α-pinene with chromyl chloride has been investigated and 11 compounds amounting to 81% of the total reaction have been isolated and identified. Besides a small amount of recovered α-pinene these compounds have been found to be products of acid-catalyzed rearrangement (bornyl chlorid...
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| Veröffentlicht in: | Canadian journal of chemistry 1972-12, Vol.50 (24), p.4022-4028 |
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| Sprache: | eng |
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| container_end_page | 4028 |
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| container_issue | 24 |
| container_start_page | 4022 |
| container_title | Canadian journal of chemistry |
| container_volume | 50 |
| creator | Bachelor, Frank William Cheriyan, Ukken Ouseph |
| description | The oxidation of α-pinene with chromyl chloride has been investigated and 11 compounds amounting to 81% of the total reaction have been isolated and identified. Besides a small amount of recovered α-pinene these compounds have been found to be products of acid-catalyzed rearrangement (bornyl chloride, borneol, and limonene); products of allylic oxidation (myrtenal, myrtenol, and verbenone); and products of oxidative addition-rearrangement (pinocamphone, pinocarveol, campholenaldehyde, and pinol). In addition, p-cymene was isolated which may arise from several oxidation sequences. The isolation of optically active pinol suggests that at least part of the oxidation of α-pinene is initiated by attack of the chromyl chloride on the same side of the double bond as the dimethyl substituted bridge. An attack by a positive chromium atom on the double bond is ruled out by a deuteration study. |
| doi_str_mv | 10.1139/v72-635 |
| format | Article |
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Besides a small amount of recovered α-pinene these compounds have been found to be products of acid-catalyzed rearrangement (bornyl chloride, borneol, and limonene); products of allylic oxidation (myrtenal, myrtenol, and verbenone); and products of oxidative addition-rearrangement (pinocamphone, pinocarveol, campholenaldehyde, and pinol). In addition, p-cymene was isolated which may arise from several oxidation sequences. The isolation of optically active pinol suggests that at least part of the oxidation of α-pinene is initiated by attack of the chromyl chloride on the same side of the double bond as the dimethyl substituted bridge. 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Besides a small amount of recovered α-pinene these compounds have been found to be products of acid-catalyzed rearrangement (bornyl chloride, borneol, and limonene); products of allylic oxidation (myrtenal, myrtenol, and verbenone); and products of oxidative addition-rearrangement (pinocamphone, pinocarveol, campholenaldehyde, and pinol). In addition, p-cymene was isolated which may arise from several oxidation sequences. The isolation of optically active pinol suggests that at least part of the oxidation of α-pinene is initiated by attack of the chromyl chloride on the same side of the double bond as the dimethyl substituted bridge. An attack by a positive chromium atom on the double bond is ruled out by a deuteration study.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v72-635</doi><tpages>7</tpages></addata></record> |
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| ispartof | Canadian journal of chemistry, 1972-12, Vol.50 (24), p.4022-4028 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_crossref_primary_10_1139_v72_635 |
| source | NRC Research Press; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| title | The Chromyl Chloride Oxidation of α-Pinene |
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