L. L. Bambas, Parke, Davis and Company, Detroit, Michigan.

• Preface viiPart I—Thiadiazoles, Their Derivatives and Selenium Analogs Derivatives of the 1,2,3-Thiadiazoles and Their Selenium Analogs 31.2.3- Thiadiazoles 3∆2,2,3-Thiadiazoline-S-dioxides 91.2.3- Benzothiadiazoles 10Discussion 16Naphthothiadiazoles 31Benzoselenadiazoles 31Derivatives of the 1,2,4-Thiadiazoles and Their Selenium Analogs 351.2.4- Thiadiazoles 35I. Derivatives of Perthiocyanic and Isoperthiocyanic Acids 35Discussion 44II. 3-and 5-Aryl Substituted 1,2,4-Thiadiazoles 51III. 1,2,4-Thiadiazolidines (Especially the 3,5-Bis(imino) Derivatives) 541.2.4- Selenadiazoles 80Derivatives of the 1,3,4-Thiadiazoles and Their Selenium Analogs 811.3.4- Thiadiazoles 812,5- Dialkyl- and the 2,5-Diaryl-1,3,4-thiadiazoles 81∆2-1,3,4-Thiadiazolines 89Glycothiadiazolines or the 2,4-Diphenyl-5-poIyhydroxyalkyl-∆2-1,3,4- thiadiazolines 97Discussion 1022- Amino-1,3,4-thiadiazoles and the 5-Imino-∆2-1,3,4-thiadiazolines 1035-Imino-∆2,-1,3,4-thiadiazolines, 1,3,4-Thiadiazol-5(4)-onesand 1,3,4-Thiadiazol-5(4)-thiones 1152-Mercapto-∆2-1,3,4-thiadiazolines 1202,5- Diamino-1,3,4-thiadiazoles and Their Derivatives 124Discussion of the Chemistry of the 2,5-Diamino-1,3,4-thiadiazoles 1322-Amino-5-imino-∆2-1,3,4-thiadiazolines and Their Derivatives 1412-Amino-5-mercapto-1,3,4-thiadiazoles and Related Compounds 143Discussion 1512-Amino-∆2-1,3,4-thiadiazol-5(4)-ones 159Discussion 1632-Amino-3- and -4-Substituted-1,3,4-thiadiazol-5(4)-ones and Related Compounds 167Discussion 1732.5- Dimercapto-1,3,4-thiadiazoIe, 2-Mercapto-1,3,4-thiadiazol-5(4)-thiones and Related Compounds 177Discussion 1852-Carboxy-5-thioxo-∆2-1,3,4-thiadiazolines 1995.6- Dithia-2,3-diazabicyclo [2.1.1]hex-3-enes, 5-Thia-2,3,6-triazabicyclo [2.1.1]-hex-3-enes, and Related ∆2-1,3,4-Thiadiazolines or ψ-1,3,4-Thiadiazoles 2001,3,4- Selenadiazoles 202Derivatives of the 2,1,3-Thiadiazoles and Their Selenium Analogs 2052,1,3- Benzothiadiazoles, 2,1,3-Benzoselenadiazoles, and Related Compounds 205Discussion 2074.7- Methanobenzisothiadiazoles 211Part II—Five-Membered Rings Containing Nitrogen, Sulfur, Selenium, or Oxygen Atoms in Addition to One Sulfur and One Nitrogen1.2.3- Benzodithiazoles, Benzo-2,3-thiaza-1-thionium Chlorides, and Benzo-1,3-thiaza-2-thionium Chlorides 2151.3.2- Benzodisulfonazole 2171.3.4- Dithiazoles 2171.2.3.4- Dithiadiazoles 218Condensed Systems Containing 1,2,3,4-Dithiadiazoles 2191.2.3.4- ThiatriazoIes 2191.2.3- Oxathiazole-S-oxides or 1,2,3-Oxasulfinazoles 2201,4,2- Oxathiazoles 2217-Nitroso-∆3,7-dihydrobenz-2,1,3-oxaselenazoles 222Part III—Isothiazoles, Their Derivatives and Selenium Analogs2.1- Benzisothiazoles 2251.2- Benzisothiazoles, Their Homologs and Selenium Analogs 2271.2- Benzisothiazoles 227Discussion 2313,3'-Bis( 1,2-benzisothiazoline) 238Naphth[2.3-d]isothiazoles and the Naphth[1.2-d]isothiazoles 2382.3- Dihydrobenz[d]imidazo[1.2-b]isothiazole 239Discussion 2426-Anthr[9.1]isothiazoles and Related Compounds 2456-Anthr[9.1]isoselenazoles 2501.2- Benzisothiazolium Compounds 2501.2- Benzisothiazol-3(2)-ones 253Discussion 2641.2- Benzisothiazol-3(2)-thiones 2711.2- Benzisoselenazol-3(2)-ones 2731.2- Benzisothiazol-3(2)-one S-oxides 2741,2- Benzisosulfonazoles, Their Homologs and Derivatives 2782,3- Dihydro-1,2-benzisosulfonazoles or 2,3-Dihydro-1,2-benzisothiazole-S-dioxides 278Discussion 2871,2- Benzisosulfonazoles 2973- Amino-1,2-benzisosulfonazoles or 3-Imino-2,3-dihydro-1,2-benzisosulfonazoles 302Saccharin, Benzoic Sulfinide, or 2,3-Dihydro-1,2-benzisosuIfonazol-3-one 318Discussion 3252-Substituted Saccharins 327Thiosaccharin or 2,3-Dihydro-1,2-benzisosulfonazol-3(2)-thione 340Saccharin Derivatives Substituted in the Benzene Ring or the 2,3-Dihydro-,1,2-Benzisosulfonazol-3(2)-ones and Condensed Systems 3421,8- Naphthosultams or the 2-, 3-, and 5-Naphth[1.8-cd]isosulfonazoles 3544- [1.2]Benzisosulfonazolo[4.3-ab]phenazines and the 6-[1.2]Benzisosulfonazolo-[4.3-ab]phenazines 37010-Camphorsulfonanhydramide and Related Compounds 373Index 379

L. L. Bambas, Parke, Davis and Company, Detroit, Michigan.

• Preface viiPart I—Thiadiazoles, Their Derivatives and Selenium Analogs Derivatives of the 1,2,3-Thiadiazoles and Their Selenium Analogs 31.2.3- Thiadiazoles 3∆2,2,3-Thiadiazoline-S-dioxides 91.2.3- Benzothiadiazoles 10Discussion 16Naphthothiadiazoles 31Benzoselenadiazoles 31Derivatives of the 1,2,4-Thiadiazoles and Their Selenium Analogs 351.2.4- Thiadiazoles 35I. Derivatives of Perthiocyanic and Isoperthiocyanic Acids 35Discussion 44II. 3-and 5-Aryl Substituted 1,2,4-Thiadiazoles 51III. 1,2,4-Thiadiazolidines (Especially the 3,5-Bis(imino) Derivatives) 541.2.4- Selenadiazoles 80Derivatives of the 1,3,4-Thiadiazoles and Their Selenium Analogs 811.3.4- Thiadiazoles 812,5- Dialkyl- and the 2,5-Diaryl-1,3,4-thiadiazoles 81∆2-1,3,4-Thiadiazolines 89Glycothiadiazolines or the 2,4-Diphenyl-5-poIyhydroxyalkyl-∆2-1,3,4- thiadiazolines 97Discussion 1022- Amino-1,3,4-thiadiazoles and the 5-Imino-∆2-1,3,4-thiadiazolines 1035-Imino-∆2,-1,3,4-thiadiazolines, 1,3,4-Thiadiazol-5(4)-onesand 1,3,4-Thiadiazol-5(4)-thiones 1152-Mercapto-∆2-1,3,4-thiadiazolines 1202,5- Diamino-1,3,4-thiadiazoles and Their Derivatives 124Discussion of the Chemistry of the 2,5-Diamino-1,3,4-thiadiazoles 1322-Amino-5-imino-∆2-1,3,4-thiadiazolines and Their Derivatives 1412-Amino-5-mercapto-1,3,4-thiadiazoles and Related Compounds 143Discussion 1512-Amino-∆2-1,3,4-thiadiazol-5(4)-ones 159Discussion 1632-Amino-3- and -4-Substituted-1,3,4-thiadiazol-5(4)-ones and Related Compounds 167Discussion 1732.5- Dimercapto-1,3,4-thiadiazoIe, 2-Mercapto-1,3,4-thiadiazol-5(4)-thiones and Related Compounds 177Discussion 1852-Carboxy-5-thioxo-∆2-1,3,4-thiadiazolines 1995.6- Dithia-2,3-diazabicyclo [2.1.1]hex-3-enes, 5-Thia-2,3,6-triazabicyclo [2.1.1]-hex-3-enes, and Related ∆2-1,3,4-Thiadiazolines or ψ-1,3,4-Thiadiazoles 2001,3,4- Selenadiazoles 202Derivatives of the 2,1,3-Thiadiazoles and Their Selenium Analogs 2052,1,3- Benzothiadiazoles, 2,1,3-Benzoselenadiazoles, and Related Compounds 205Discussion 2074.7- Methanobenzisothiadiazoles 211Part II—Five-Membered Rings Containing Nitrogen, Sulfur, Selenium, or Oxygen Atoms in Addition to One Sulfur and One Nitrogen1.2.3- Benzodithiazoles, Benzo-2,3-thiaza-1-thionium Chlorides, and Benzo-1,3-thiaza-2-thionium Chlorides 2151.3.2- Benzodisulfonazole 2171.3.4- Dithiazoles 2171.2.3.4- Dithiadiazoles 218Condensed Systems Containing 1,2,3,4-Dithiadiazoles 2191.2.3.4- ThiatriazoIes 2191.2.3- Oxathiazole-S-oxides or 1,2,3-Oxasulfinazoles 2201,4,2- Oxathiazoles 2217-Nitroso-∆3,7-dihydrobenz-2,1,3-oxaselenazoles 222Part III—Isothiazoles, Their Derivatives and Selenium Analogs2.1- Benzisothiazoles 2251.2- Benzisothiazoles, Their Homologs and Selenium Analogs 2271.2- Benzisothiazoles 227Discussion 2313,3'-Bis( 1,2-benzisothiazoline) 238Naphth[2.3-d]isothiazoles and the Naphth[1.2-d]isothiazoles 2382.3- Dihydrobenz[d]imidazo[1.2-b]isothiazole 239Discussion 2426-Anthr[9.1]isothiazoles and Related Compounds 2456-Anthr[9.1]isoselenazoles 2501.2- Benzisothiazolium Compounds 2501.2- Benzisothiazol-3(2)-ones 253Discussion 2641.2- Benzisothiazol-3(2)-thiones 2711.2- Benzisoselenazol-3(2)-ones 2731.2- Benzisothiazol-3(2)-one S-oxides 2741,2- Benzisosulfonazoles, Their Homologs and Derivatives 2782,3- Dihydro-1,2-benzisosulfonazoles or 2,3-Dihydro-1,2-benzisothiazole-S-dioxides 278Discussion 2871,2- Benzisosulfonazoles 2973- Amino-1,2-benzisosulfonazoles or 3-Imino-2,3-dihydro-1,2-benzisosulfonazoles 302Saccharin, Benzoic Sulfinide, or 2,3-Dihydro-1,2-benzisosuIfonazol-3-one 318Discussion 3252-Substituted Saccharins 327Thiosaccharin or 2,3-Dihydro-1,2-benzisosulfonazol-3(2)-thione 340Saccharin Derivatives Substituted in the Benzene Ring or the 2,3-Dihydro-,1,2-Benzisosulfonazol-3(2)-ones and Condensed Systems 3421,8- Naphthosultams or the 2-, 3-, and 5-Naphth[1.8-cd]isosulfonazoles 3544- [1.2]Benzisosulfonazolo[4.3-ab]phenazines and the 6-[1.2]Benzisosulfonazolo-[4.3-ab]phenazines 37010-Camphorsulfonanhydramide and Related Compounds 373Index 379

L. L. Bambas, Parke, Davis and Company, Detroit, Michigan.

• Preface viiPart I—Thiadiazoles, Their Derivatives and Selenium Analogs Derivatives of the 1,2,3-Thiadiazoles and Their Selenium Analogs 31.2.3- Thiadiazoles 3∆2,2,3-Thiadiazoline-S-dioxides 91.2.3- Benzothiadiazoles 10Discussion 16Naphthothiadiazoles 31Benzoselenadiazoles 31Derivatives of the 1,2,4-Thiadiazoles and Their Selenium Analogs 351.2.4- Thiadiazoles 35I. Derivatives of Perthiocyanic and Isoperthiocyanic Acids 35Discussion 44II. 3-and 5-Aryl Substituted 1,2,4-Thiadiazoles 51III. 1,2,4-Thiadiazolidines (Especially the 3,5-Bis(imino) Derivatives) 541.2.4- Selenadiazoles 80Derivatives of the 1,3,4-Thiadiazoles and Their Selenium Analogs 811.3.4- Thiadiazoles 812,5- Dialkyl- and the 2,5-Diaryl-1,3,4-thiadiazoles 81∆2-1,3,4-Thiadiazolines 89Glycothiadiazolines or the 2,4-Diphenyl-5-poIyhydroxyalkyl-∆2-1,3,4- thiadiazolines 97Discussion 1022- Amino-1,3,4-thiadiazoles and the 5-Imino-∆2-1,3,4-thiadiazolines 1035-Imino-∆2,-1,3,4-thiadiazolines, 1,3,4-Thiadiazol-5(4)-onesand 1,3,4-Thiadiazol-5(4)-thiones 1152-Mercapto-∆2-1,3,4-thiadiazolines 1202,5- Diamino-1,3,4-thiadiazoles and Their Derivatives 124Discussion of the Chemistry of the 2,5-Diamino-1,3,4-thiadiazoles 1322-Amino-5-imino-∆2-1,3,4-thiadiazolines and Their Derivatives 1412-Amino-5-mercapto-1,3,4-thiadiazoles and Related Compounds 143Discussion 1512-Amino-∆2-1,3,4-thiadiazol-5(4)-ones 159Discussion 1632-Amino-3- and -4-Substituted-1,3,4-thiadiazol-5(4)-ones and Related Compounds 167Discussion 1732.5- Dimercapto-1,3,4-thiadiazoIe, 2-Mercapto-1,3,4-thiadiazol-5(4)-thiones and Related Compounds 177Discussion 1852-Carboxy-5-thioxo-∆2-1,3,4-thiadiazolines 1995.6- Dithia-2,3-diazabicyclo [2.1.1]hex-3-enes, 5-Thia-2,3,6-triazabicyclo [2.1.1]-hex-3-enes, and Related ∆2-1,3,4-Thiadiazolines or ψ-1,3,4-Thiadiazoles 2001,3,4- Selenadiazoles 202Derivatives of the 2,1,3-Thiadiazoles and Their Selenium Analogs 2052,1,3- Benzothiadiazoles, 2,1,3-Benzoselenadiazoles, and Related Compounds 205Discussion 2074.7- Methanobenzisothiadiazoles 211Part II—Five-Membered Rings Containing Nitrogen, Sulfur, Selenium, or Oxygen Atoms in Addition to One Sulfur and One Nitrogen1.2.3- Benzodithiazoles, Benzo-2,3-thiaza-1-thionium Chlorides, and Benzo-1,3-thiaza-2-thionium Chlorides 2151.3.2- Benzodisulfonazole 2171.3.4- Dithiazoles 2171.2.3.4- Dithiadiazoles 218Condensed Systems Containing 1,2,3,4-Dithiadiazoles 2191.2.3.4- ThiatriazoIes 2191.2.3- Oxathiazole-S-oxides or 1,2,3-Oxasulfinazoles 2201,4,2- Oxathiazoles 2217-Nitroso-∆3,7-dihydrobenz-2,1,3-oxaselenazoles 222Part III—Isothiazoles, Their Derivatives and Selenium Analogs2.1- Benzisothiazoles 2251.2- Benzisothiazoles, Their Homologs and Selenium Analogs 2271.2- Benzisothiazoles 227Discussion 2313,3'-Bis( 1,2-benzisothiazoline) 238Naphth[2.3-d]isothiazoles and the Naphth[1.2-d]isothiazoles 2382.3- Dihydrobenz[d]imidazo[1.2-b]isothiazole 239Discussion 2426-Anthr[9.1]isothiazoles and Related Compounds 2456-Anthr[9.1]isoselenazoles 2501.2- Benzisothiazolium Compounds 2501.2- Benzisothiazol-3(2)-ones 253Discussion 2641.2- Benzisothiazol-3(2)-thiones 2711.2- Benzisoselenazol-3(2)-ones 2731.2- Benzisothiazol-3(2)-one S-oxides 2741,2- Benzisosulfonazoles, Their Homologs and Derivatives 2782,3- Dihydro-1,2-benzisosulfonazoles or 2,3-Dihydro-1,2-benzisothiazole-S-dioxides 278Discussion 2871,2- Benzisosulfonazoles 2973- Amino-1,2-benzisosulfonazoles or 3-Imino-2,3-dihydro-1,2-benzisosulfonazoles 302Saccharin, Benzoic Sulfinide, or 2,3-Dihydro-1,2-benzisosuIfonazol-3-one 318Discussion 3252-Substituted Saccharins 327Thiosaccharin or 2,3-Dihydro-1,2-benzisosulfonazol-3(2)-thione 340Saccharin Derivatives Substituted in the Benzene Ring or the 2,3-Dihydro-,1,2-Benzisosulfonazol-3(2)-ones and Condensed Systems 3421,8- Naphthosultams or the 2-, 3-, and 5-Naphth[1.8-cd]isosulfonazoles 3544- [1.2]Benzisosulfonazolo[4.3-ab]phenazines and the 6-[1.2]Benzisosulfonazolo-[4.3-ab]phenazines 37010-Camphorsulfonanhydramide and Related Compounds 373Index 379