Stereochemistry of the reaction of D(positive)-2,3-epoxybutane with alcohols. The coordination reaction between silver ion and alkynes. Some relationships of sterols to plant growth

• Main Author: Helmkamp, George Kenneth
• Format: Others
• Published: 1953
• Online Access: https://thesis.library.caltech.edu/1671/1/Helmkamp_gk_1953.pdf; Helmkamp, George Kenneth (1953) Stereochemistry of the reaction of D(positive)-2,3-epoxybutane with alcohols. The coordination reaction between silver ion and alkynes. Some relationships of sterols to plant growth. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/2VN2-KE23. https://resolver.caltech.edu/CaltechETD:etd-05082003-105201 <https://resolver.caltech.edu/CaltechETD:etd-05082003-105201>

PART I. The reaction between D(+)-2,3-epoxybutane and alcohols is accompanied by a Walden inversion. The 3-methoxy-2-butanol prepared in this manner is an erythro-isomer, for meso-2,3-dimethoxybutane can be prepared from it by the Williamson synthesis. PART II. Permanganate oxidation under alkaline conditions has been employed as a method for the quantitative determination of aqueous solutions of 3-hexyne. 3-Hexyne and several homologs (methyl groups in the 1-, 2- and 5-positions) have been synthesized. Argentation constants for these have been evaluated by means of their solubilities in aqueous solutions of silver ion at constant ionic strength. PART III. A survey has been made concerning the effect of various steroidal substances on growth of pea embryos. A strong inhibition was noted in the presence of testosterone. Estrone and saponins tended to enhance early growth.