A investigations in the vitamin A‐series. II. Allylic rearrangements in the vitamin A‐series
- 1 January 1952
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 71 (9) , 899-919
- https://doi.org/10.1002/recl.19520710908
Abstract
By splitting off water from the intermediate hydroxy‐compounds in the Vitamin A‐series allylic rearrangement takes place into the cyclohexene ring. This rearrangement occurs throughout the whole Vitamin‐A‐series‐ with those hydroxy‐intermediates wherein the hydroxy‐group is in an allyl position with regard to the double bond in the cyclohexene ring.The reason why so many attempts to prepare synthetic Vitamin A in reasonable yields, starting with “key” intermediates other than the C14aldehyde, lead to a failure, has been outlined.Keywords
This publication has 14 references indexed in Scilit:
- Synthesis of Vitamin AJournal of the American Chemical Society, 1951
- Investigations in the vitamin‐A series. I. A new synthesis of vitamin‐A acid and vitamin‐A: (Preliminary communication)Recueil des Travaux Chimiques des Pays-Bas, 1950
- Zur cis‐trans‐Isomerisierung von CarotinoidenHelvetica Chimica Acta, 1949
- SYNTHESIS OF VITAMIN AJournal of the American Chemical Society, 1949
- Zur Synthese des Vitamins A. 1. Mitteilung. Eine neue Methode zur direkten Darstellung von Vitamin A von hoher biologischer WirksamkeitHelvetica Chimica Acta, 1949
- 68. Studies in the polyene series. Part XXV. Molecular structure and vitamin-A activity. The synthesis of a biologically active C17 acidJournal of the Chemical Society, 1949
- Recent developments in the vitamin A fieldJournal of the Chemical Society, 1948
- A NEW SYNTHESIS OF 1-(2',6',6'-TRIMETHYLCYCLOHEXEN-1'-YL)-3-METHYLHEXA-1,3,5-TRIEN- 7-ONE (C18 KETONE)Journal of the American Chemical Society, 1947
- The Synthesis of Certain Unsaturated Compounds from Beta-Ionone and Tetrahydroionone1,2,3Journal of the American Chemical Society, 1935
- Über mehrfach ungesättigte, den β‐ order α‐Jononkohlenstoffring enthaltende VerbindungenHelvetica Chimica Acta, 1932