I. The Structures of Phytotoxic Compounds from Thamnosma Montana. II. The Action of Phytotoxic Compounds on Plants. III. Preparation and Reactions of S-Phenylthiolcarbamates. IV. Studies on the Synthesis of Actidione

Citation

Crosby, Donald Gibson (1954) I. The Structures of Phytotoxic Compounds from Thamnosma Montana. II. The Action of Phytotoxic Compounds on Plants. III. Preparation and Reactions of S-Phenylthiolcarbamates. IV. Studies on the Synthesis of Actidione. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/T35B-D641. https://resolver.caltech.edu/CaltechETD:etd-12042003-095430

Abstract

The chemistry of the three phytotoxic compounds isolated from Thamnosma montana by E.L. Bennett in 1949 has been studied, and two of the substances have been identified as the known furocoumarins isopimpinellin and byakangelicin. Degradation and partial synthesis of the third compound have shown that it is also a furocoumarin, and have indicated its probable structure. The effects of several naturally-occurring phytotoxic substances on plants have been observed under controlled conditions, and have been compared with the effects noted in nature. The mechanism of the toxic action is still ambiguous. Convenient methods for the synthesis of S-substituted thiolcarbamates have been found, and the scope and limitations of their reactions with primary and secondary amines, amides, and hydrazines to produce ureas, acylureas, and semicarbazides, respectively, have been determined. The mechanism of the general reaction and its application to the identification of organic compounds also have been considered. Attempts have been made to synthesize the antibiotic substance "Actidione" by four different routes, and although this end has not been achieved, much groundwork has been laid for the eventual preparation of the compound.

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