1026493-35-5

Basic information

• Product Name: phenyl <1-tert-butoxycarbonyl-4-(trimethylsilyl)-1H-pyrrole-3-yl>iodonium triflate
• CAS NO: 1026493-35-5
• Molecular Weight: 591.462
• Mol File: 1026493-35-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: phenyl <1-tert-butoxycarbonyl-4-(trimethylsilyl)-1H-pyrrole-3-yl>iodonium triflate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl <1-tert-butoxycarbonyl-4-(trimethylsilyl)-1H-pyrrole-3-yl>iodonium triflate(1026493-35-5)
• EPA Substance Registry System: phenyl <1-tert-butoxycarbonyl-4-(trimethylsilyl)-1H-pyrrole-3-yl>iodonium triflate(1026493-35-5)

Safety Data

• Hazardous Substances Data: 1026493-35-5(Hazardous Substances Data)

Upstream product

• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 195820-64-5 1,3,4-tris(trimethylsilyl)-1H-pyrrole 
• 195820-65-6 3,4-bis(trimethylsilyl)-1H-pyrrole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 536-80-1 iodosylbenzene 
• 2926-30-9 sodium triflate 
• 195820-66-7 1-(tert-butoxycarbonyl)-3,4-bis(trimethylsilyl)-1H-pyrrole 

Relevant articles and documents

Generation and trapping reactions of 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole

3,4-Bis(trimethylsilyl)-1H-pyrrole (5) was employed as a key precursor to generate a highly strained and reactive five-membered cyclic cumulene, namely 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole (4). The transient existence of 4 at room temperature was confirmed by trapping reactions with furan, acrylonitrile, and benzene, affording cycloadducts 13-15. The choice of the electron-withdrawing tert-butoxycarbonyl group as the N-substituent was essential because it was able to adjust the electron density of 11a and 11b. As a result, monoiodonium triflates 12a and 12b were obtained, respectively. On the contrary, N-tert-butyl-3,4-bis(trimethylsilyl)-1H-pyrrole (9) led instead to the bisiodonium triflate 10 upon treatment with the Zefirov reagent.