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Cumulenes in Click Reactions

Henri Ulrich

ISBN: 978-0-470-77932-3 December 2009 562 Pages


Cumulenes are organic molecules with two or more cumulative (consecutive) double bonds. Their reactions often proceed at room temperature, with or without a catalyst, and are stereospecific, giving the reaction products in high yields – features characteristic of “click reactions”. 

Cumulenes in Click Reactions presents a comprehensive list of cumulene systems and their reactions, with an emphasis on their “click-like” nature. The chapters are structured according to the number of carbon atoms in the system, including coverage of:

  • introduction to the chemistry of cumulenes
  • one-carbon cumulenes: sulfines, sulfenes, thiocarbonyl S-imides, thiocarbonyl S-sulfides, and 1-aza-2-azoniaallene salts
  • two-carbon cumulenes: carbon oxides, carbon sulfides, carbon nitrides (isocyanates, isothiocyanates, and carbodiimides), phosphaallenes, and diarsaallenes
  • 1,2-dicarbon cumulenes: ketenes, thioketenes, ketenimines, 1-silaallenes, 1-phosphaallenes, and other metal allenes
  • 1,3-dicarbon cumulenes: thiocarbonyl S-ylides, 2-azaallenium salts, 1-oxa-3-azoniabutatriene salts, 1-thia-3-azoniabutatriene salts, and phosphorous ylides
  • 1,2,3-tricarbon cumulenes: allenes, butatrienes, higher cumulenes and heterobutatrienes
  • noncarbon cumulenes: azides, triazaallenium salts, sulfur oxides, sulfur nitrides, N-sulfinylamines, sulfurdiimides, and dithionitronium cation

Cumulenes in Click Reactionsis an essential guide for researchers and advanced students in academia and research working in synthetic organic, inorganic and bioorganic chemistry.



1 General Introduction


2 1-Carbon Cumulenes

2.1 Sulfines, R2C SO

2.2 Sulfenes, R2C S(O)O

2.3 Other 1-Carbon Cumulenes

3 2-Carbon Cumulenes

3.1 Carbon Oxides, O C O, :CO

3.2 Carbon Sulfides, S C S, S CO

3.3 Carbon Nitrides

3.4 Center Carbon Phosphorallenes, P C P

4 1,2-Dicarbon Cumulenes

4.1 Ketenes, R2C C O

4.2 Thioketenes, R2C C S

4.3 Ketenimines, R2C C NR

4.4 1-Silaallenes, R2C C Si

4.5 1-Phosphaallenes, R2C C P

4.6 Other Metal Allenes

5 1,3-Dicarbon Cumulenes

5.1 Thiocarbonyl S-ylides, R2C S CH2

5.2 2-Azaallenium Salts, R(Ce)C N+ C(Ce)R

5.3 1-Oxa-3-azoniabutatriene Salts, R2C N+ C O

5.4 1-Thia-3-azabutatriene Salts, R2C N+ C S

5.5 Phosphorus Ylides

6 1,2,3-Tricarbon Cumulenes

6.1 Allenes, R2C CR2

6.2 [3] Cumulenes, R2C C C CR2

6.3 [4] Cumulenes, R2C C C C CR2

6.4 [5] Cumulenes, R2C C C C C CR2

7 Noncarbon Cumulenes

7.1 Azides, RN N N

7.2 Triazaallenium Salts, RN N+ NR

7.3 Sulfur Oxides

7.4 Sulfur Nitrides

7.5 Cationic Boron Cumulenes, R2N B NR