42587-61-1

Basic information

• Product Name: (1S)-bicyclo<2.2.2>oct-5-en-2-one p-toluenesulfonylhydrazone
• CAS NO: 42587-61-1
• Molecular Weight: 290.386
• Mol File: 42587-61-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S)-bicyclo<2.2.2>oct-5-en-2-one p-toluenesulfonylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-bicyclo<2.2.2>oct-5-en-2-one p-toluenesulfonylhydrazone(42587-61-1)
• EPA Substance Registry System: (1S)-bicyclo<2.2.2>oct-5-en-2-one p-toluenesulfonylhydrazone(42587-61-1)

Safety Data

• Hazardous Substances Data: 42587-61-1(Hazardous Substances Data)

Upstream product

• 2220-40-8 bicyclo[2.2.2]oct-5-en-2-one 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 34020-37-6 endo-bicyclo<2.2.2>oct-5-en-2-yl acetate 
• 6688-07-9 5-hydroxybicyclo[2.2.2]oct-2-ene 

Downstream Products

• 500-23-2 bicyclo[2.2.2]octa-2,5-diene 
• 74773-69-6 (1R,4S)-2-Methyl-bicyclo[2.2.2]octa-2,5-diene 
• 74773-69-6 (1S)-2-methylbicyclo<2.2.2>octa-2,5-diene 

Relevant articles and documents

Electronic Structure of Symmetric Homocojugated Dienes. Circular Dichroism of (1S)-2-Deuterio- and 2-Methylnorbornadiene and (1S)-2-Deuterio- and 2-Methylbicyclooctadiene

(1S)-Bicyclohepta-2,5-diene (1), (1S)-2-methylbicyclohepta-2,5-diene (3), (1S)-bicycloocta-2,5-diene (4), and (1S)-2-methylbicyclooctadiene (6) were prepared by reaction of the corresponding chiral β,γ-unsaturated ketone tosylhydrazone with CH3Li followed by either D2O or CH3I quenching.The circular dichroism Cotton effects of 1 (Δε237 = -0.032, Δε216 = +0.14, Δε205 = -0.37) and 4 (Δε222 = -0.027) are the first examples obtained from deuterated olefins or dienes whose chirality is due only to isotopic substitution.Both the deuterated and the methylated dienes exhibited multiple Cotton effects (3, Δε249 = +2.38, Δε222 = -0.25, Δε219 = -0.54, Δε214 = +0.62, Δε204 = -0.94; 6, Δε231 = +0.90, Δε211 = +0.48, Δε200 = -0.24), demonstrating the existence of interchromophoric interaction and electronic transitions that are only difficulty seen in their ultraviolet spectra.We present ab initio localized orbital RPA calculations on 1 that allow a consistent assignment of norbornadiene transitions.