66887-41-0

Basic information

• Product Name: (1S,4R,5S,6S)-5-Chloro-6-(2,4-dinitro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-ene
• CAS NO: 66887-41-0
• Molecular Weight: 326.76
• Mol File: 66887-41-0.mol

Chemical Properties

• CAS DataBase Reference: (1S,4R,5S,6S)-5-Chloro-6-(2,4-dinitro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R,5S,6S)-5-Chloro-6-(2,4-dinitro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-ene(66887-41-0)
• EPA Substance Registry System: (1S,4R,5S,6S)-5-Chloro-6-(2,4-dinitro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-ene(66887-41-0)

Safety Data

• Hazardous Substances Data: 66887-41-0(Hazardous Substances Data)

Upstream product

• 528-76-7 2,4-dinitrobenzenesulfenyl chloride 
• 278-06-8 quadricyclo[2.2.1.0.0]heptane 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 64-19-7 acetic acid 
• 278-06-8 tetracyclo-[3.2.0.0.^2,7.0^4,6]heptane 

Relevant articles and documents

Reaction of 2,4-Dinitrobenzenesulfenyl Chloride with Quadricyclene

The treatment of quadricyclene with 2,4-dinitrobenzenesulfenyl chloride has been reinvestigated and chloro adducts 1-A and 2b-A as well as acetates 4a-A, 4b-A, 6, and 7 have been obtained.Establishing 2b-A with endo-chloride led to important conclusion that endo-chloride attack occurs by collapse of ion pair.Monitoring changes in the proportions of acetates, especially with added LiClO4, has allowed conclusions about the degree of development of the carbocation intermediates.These conclusions were proposed on the basis of the previously published ideas of stereocontrol by an ion pair.

REACTION OF ARENESULFENYL CHLORIDES WITH NORBORNADIENE

The reaction of o-nitro- and 2,4-dinitrobenzenesulfenyl chlorides with norbornadiene in carbon tetrachloride leads to the preferential formation of trans-2-endo-chloro-3-exo-(arylthio)norbornene with exo attack by the sulfenyl chloride.In acetic acid the main product is 5-(arylthio)-3-chloronortricyclene, which is obtained as a result of homoallylic participation of the second double bond; its structure and configuration were established by x-ray crystallographic analysis.In both cases the formation of trans-2-exo-chloro-3-endo-(arylthio)norbornene was also observed.Under "doping-addition" conditions (AcOH + LiClO4) the reaction occurs mainly with participation of the solvent in the concluding stage, and the products are the stereoisomeric nortricyclene acetoxy sulfides.The application of the previously proposed concept of stereochemical control of the configuration of the product in an ion-pair mechanism is discussed for the case of the investigated reactions.

Electrophilic cleavage of cyclopropanes. II. Concerning the effect of increasing electron demand upon the product-determining transition state in the reaction of 4-substituted-2-nitrobenzenesulphenyl chlorides and benzenesulphenyl chlorides with tetracyclo2,7.04,6>heptane....

The effect of increasing electron demand upon the product-determining transition state in the reaction of arenesulphenyl chlorides with tetracyclo2,7.04,6>heptane has been investigated.As the electron donating ability of the remote substituents on the phenyl ring of the sulphenyl chloride is varied from nitro to methoxy the relative proportion of adducts derived from edge-on attack is found to increase relative to that of adducts derived from corner attack.An ortho-nitro group was found to lead to a stabilizing interaction only in the case of 2,4-dinitrobenzenesulphenyl chloride.A mechanism involving the competition between the two conceptual modes of approach is suggested.