Paper
Mechanistic Insights into an Unexpected Carbon Dioxide Insertion Reaction through the Crystal Structures of Carbamic Diphenylthiophosphinic Anhydride and l-[(4-Nitrophenyl)-sulfonyl]-trans-2,5-pyrrolidinedicarboxylic Acid Methyl Ester
Published Aug 26, 2010 · M. Shi, Yu-mei Shen, Jian‐Kang Jiang
Chinese Journal of Chemistry
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Abstract
The crystal structures of an unexpected carbon dioxide inserted carbamicdiphenylthiophosphinic anhydride and 1-[(4-mitrophenyl) sulfonyl]-trans-2,5-pyrrolidinedicarboxylic acid methyl ester were determined by X-ray analysis. They crystallized in the space group P2^1(#4) with a =0.9550(2), b-0.9401(4), c=1.2880(2) nm, β=107.74°, V=1.1013(5) nm~3, D calcd=1.349g/cm~3, Z=2 and P2^12^1`2^1(#19) with a=1.4666(2), b=0.7195(2), c=1.6339(2) nm, V=1.7240(7)nm~3, C calcd=1.434g/cm, Z=4, respectively. Through the investigation of these two crystal structures, the mechanistic insights into this unexpected carbon dioxide insertion in the reaction of trans-2,5-disubstituted pyrrolidine with diphenylthiophosphoryl chloride in the presence of potassium carbonate were disclosed.
The crystal structures of carbamic diphenylthiophosphinic anhydride and 1-[(4-mitrophenyl) sulfonyl]-trans-2,5-pyrrolidinedicarboxylic acid methyl ester provide insights into the unexpected carbon dioxide insertion in
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