80594-22-5

Upstream product

• 536-74-3 phenylacetylene 
• 52751-11-8 cis<α,β-2H2>styrene 
• 186581-53-3 diazomethane 
• 80594-21-4 (+)-(1S,2S,3S)-t-2-phenyl-1,2,c-3-trideuteriocyclopropanecarboxylic acid 

Downstream Products

• 88546-83-2 (1S,2S,3S)-t-2-phenyl-1,2,c-3-trideuteriocyclopropanecarboxaldehyde 
• 88546-86-5 (2R,3R)-1-phenyl-r-1,c-2,t-3-trideuteriocyclopropane 
• 80594-26-9 (+)-(1S,2S,3S)-t-2-phenyl-1,2,c-3-trideuteriocyclopropylmethanol 
• 80594-21-4 (+)-(1S,2S,3S)-t-2-phenyl-1,2,c-3-trideuteriocyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates

Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with α-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2- phenylcyclopropanecarboxylates (the 1-d-3-13C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized. The Royal Society of Chemistry 2006.

Stereochemical Kinetics of the Thermal Stereomutations Interconverting Achiral Isomers of 1-Phenyl-1,2,3-trideuteriocyclopropane

All three achiral forms of 1-phenyl-1,2,3-trideuteriocyclopropane have been synthesized with high stereochemical integrity, and the thermal stereomutations among them have been followed at 309.3 deg C in the gas phase by Raman and 1H NMR spectroscopy.The

Complete Kinetic Analysis of the Thermal Stereomutations of (+)-(1S,2S,3R)-r-1-Cyano-t-2-methyl-1,2,t-3-trideuteriocyclopropane

(+)-(1S,2S,3R)-r-1-Cyano-t-2-methyl-1,2,t-3-trideuteriocyclopropane has been synthesized in optically pure form.The kinetic of thermal stereomutations which interconvert this and seven other isomeric cyclopropanes have been followed: at 335.4 deg C in the gas phase, the title compound undergoes stereomutations with rate constants (x105 s) k1 = 0.55, k2 = 0.61, k3 = 0.10, k12 = 0.88, k13 = 0.083, and k23 = 0; the cis-1-cyano-2-methyl-1,2,3-trideuteriocyclopropanes exhibit stereomutation rate constants (x105 s) k'1 = 0.62, k'2 = 0.69, k'3 = 0.15, k'12 = 1.31, k'13 = 0.09, and k'23 = 0.While cyclopropanes 1,2-disubstituted with potent radical-stabilizing groups such as phenyl, cyano, and vinyl give stereomutation products by way of C(1)-C(2) bond cleavage only, the deuterium-labeled 1-cyano-2-methylcyclopropanes experience thermal stereomutations consistent with the intermediacy of two distinct trimethylene diradicals, one formed through cleavage of the C(1)-C(2) bond, the other by breaking C(1)-C(3).