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Investigation of Synthetic Routes Towards, and Reactions of, 2,3-Disubstituted-1, 4-Dioxans.

Pearson, Ronald George. (1959) Investigation of Synthetic Routes Towards, and Reactions of, 2,3-Disubstituted-1, 4-Dioxans. Doctoral thesis, University of Surrey (United Kingdom)..

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Attempted syntheses of the stereoisomeric 2,3-dicarboxy-1,4-dioxans have been made, using methods adapted from the preparation of ethers, and also by substitution of the chlorine atoms in trans-2,5-dichloro-1,4-dioxan. The former method involved the Williamson type of ether synthesis, and also the use of silver oxide (Purdie's method). This method was also applied in the attempted preparation of 2,3-diphenyl-1,4-dioxan, the cis- and trans- isomers of which are known. From the complex mixture of products from the chlorinations of trans-2,3-ethylenedioxy-l,4-dioxan have been isolated both di(2-chloroethyl) oxalate and ethylene oxalate. This is readily accounted for by the assumption that the chlorination leads to trans-2,3-dichloro-2,3-ethylenedioxy-1,4-dioxan, which then undergoes a rearrangement reaction analogous to that already observed with a-chloro-ethers. A third expected rearrangement product, 1,2-dichloroethane was not isolated. It has been shown that the rearrangement, in the present instance, is a thermal one, and it is unlikely that the intermediate, trans-2,3-dichloro-2,3-ethylenedioxy-l,4-dioxan, will be capable of isolation. Bromination of the ethylenedioxy-dioxan, by means of N-bromosuccinimide, afforded di(2- bromoethyl) oxalate only. The oxalates were compared directly (m.p., mixed m.p., infra-red absorption spectra) with authentic esters prepared for the purpose by alternative procedures. The structure of a product, hitherto uninvestigated, from the interaction of trons-2,3-dichloro-1,4-dioxan and diethyl (+)-tartrate, has been limited to three possibilities.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
Pearson, Ronald George.
Date : 1959
Contributors :
Additional Information : Thesis (Ph.D.)--University of Surrey (United Kingdom), 1959.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 15:15
Last Modified : 06 Nov 2018 16:54

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