57981-01-8

Usage

Molecular class

Isoindoline-1,3-diones

Derivative

Contains a perfluorophenyl group and a methoxy group attached to the isoindoline ring

Usage

Materials science and organic chemistry

Potential applications

Various organic reactions and as a building block for the synthesis of complex molecules

Unique features

Valuable tool for researchers in the development of new materials and chemical compounds due to its structure and composition.

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 1765-40-8 (bromomethyl)pentafluorobenzene 

Downstream Products

• 72915-12-9 O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine hydrochloride 

Relevant academic research and scientific papers

Synthesis of N-(2,3,4,5,6-pentafluorobenzyloxy)-γ-lactams by rhodium-catalyzed cyclization of diazo amides

Rhodium-catalyzed cyclization of N-(2,3,4,5,6-pentafluoro-benzyloxy) diazo amides leading to the corresponding γ-lactams is described. The cyclization is based on the intramolecular catalytic insertion into the C-H bond. Fourteen lactams were obtained with up to 91 % yield and 88 % ee. Gabapentin hydrochloride, a GABA analog, was also synthesized by this method, which shows that deprotection of the 2,3,4,5,6-pentafluorobenzyloxy group is possible. The rhodium-catalyzed cyclization of diazo amides, derived from O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine, is reported. The reaction leads to a variety of lactams in up to 91 % yield and 88 % ee. The developed method was applied in the synthesis of gabapentin hydrochloride, an important GABA analog.