ORGANIC COMPOUNDS OF ARSENIC ANTIMONY BY GILBERT T. MORGAN, D. So., F. R. S., F. I. C., M. R. I. A. 5 A. R. C. So. Professor of Applied Chemistry City and Guilds Technical College Fixsbury. Formerly Professor in the Faculty of Applied Chemistry, Royal College of Science for Ireland and Assistatit Professor in the Imperial College of Science and Technology. Corresponding Member of the Royal Dublin Society, . i-., .5 Uity, Ms, LONGMANS, GREEN, AND CO. 39 PATERNOSTER ROW, LONDON NEW YORK, BOMBAY AND CALCUTTA PREFACE ORGANIC derivatives of arsenic appeal to the scientific public for two widely different reasons. From the historical stand point these substances are of considerable interest because they have been under investigation throughout a period of time coeval with the birth and development of modern chemistry. Suc cessive generations of chemists have examined these compounds from points of view which varied with the gradual evolution of chemical science, and the results of their researches have played an important part inlhe establishment of current theories of the molecular constitution of matter. Additional importance is conferred on the subject by the circumstance that very early in the study of organic arsenical compounds it was realised that, in these synthetic products, the physician has at his disposal substances of great physiological potency. It is chiefly this medicinal attribute of organic arsenicals which has evoked the more recent activities in the synthesis of organo-metalloidal compounds. These utilitarian investigations have not been restricted to organic arsenicals, but have extended to the corresponding derivatives of antimony, and accordingly these related productsare also discussed in the present mono graph. Both series of organo-metalloidal compounds are already so extensive that a detailed description of every individual member would render this treatise unduly bulky, but a liberal selection has been made comprising those substances having either a practical application or some aspect of theoretical interest. A biblio graphy of the most important researches and treatises down to the end of 1917 has been included, and these references to original memoirs supply the necessary due to further infonnatte re gardiBg any known organic arsenical or arttimonial wifeb in the future acquire increased PREFACE It is my pleasant duty to express my grateful thanks for assistance received in the compilation of this monograph from the following firms Les fitablissements Poulenc Freres, Messrs. Burroughs Wellcome Co., and Messrs. May and Baker. I also desire to acknowledge the friendly help received from Dr. W. H. Martindale, from Mr. E. Scholl, formerly of the Farbwerke vormals Meister, Lucius, und Bnining from Mr. F. W. Clifford, Librarian of the Chemical Society and from Messrs. E. D. Evens, B. Sc., and W. R. Grist, who have assisted me in reading the proofs and in arranging the index and biblio graphic data. G. T. M. CITY AND GUILDS TECHNICAL COLLEGE, FINSBURY, LEONARD STREET, LONDON, E. C. 2. VI CONTENTS PAGE PREFACE ix INTRODUCTION xi Chemical …. ……. xi Historical xii CHAPTER I. CACODYL i Earliest Researches on Organic Arsenicals r Section I. Cadets fuming arsenical liquid I II. Cacodyl and its derivatives 5 III. Homologues of cacodyl 17 CHAPTER II. ALIPHATIC ARSENICALS AND ANTIMONIALS 20 Syntheses of Alkyl Organo-metalloidal Compounds containingArsenic and Antimony 20 Section I. General Reactions 21 II. Aliphatic arsenic compounds 32 III. Aliphatic antimony compounds …. - 53 CHAPTER III. AROMATIC ARSENICALS 64 Arylarsines and their Immediate Derivatives 64 Section I. Benzene derivatives with one aromatic nucleus attached to one arsenic atom 78 II. Benzene derivatives - with two aromatic nuclei attached to one arsenic atom 95 III . Benzene derivatives with three aromatic nuclei attached to one arsenic atom 100 IV. Toluene derivatives with one aromatic nucleus at tached to one arsenic atom - 105 V…