25181-26-4

Upstream product

• 624-64-6 trans-2-Butene 
• 908094-04-2 phenyldiazomethane 
• 590-18-1 (Z)-2-Butene 
• 108964-91-6 (1RS,2RS,3SR)-2-methyl-3-trimethylstannyl-1-phenyl-1-butanol 
• 618-31-5 benzylidene dibromide 
• 7653-96-5 r-1-phenyl-cis-2,cis-3-dimethylcyclopropane 
• 100-52-7 benzaldehyde 
• 1439-07-2 trans-Stilbene oxide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 100-44-7 benzyl chloride 

Downstream Products

• 38332-19-3 1,cis-2-Dimethyl-trans-3-(p-nitrophenyl)-cyclopropan 
• 125830-08-2 (2S*,3R*)-2-methoxy-3-methyl-4-phenylbutane 
• 125830-10-6 (2S*,3R*)-2,3-dimethyl-4-phenylbutanecarbonitrile 
• 7653-96-5 r-1-phenyl-cis-2,cis-3-dimethylcyclopropane 
• 79101-72-7 3-Methyl-4-phenylhexan 
• 7653-95-4 1,2-cis,trans-Dimetrhyl-3-phenylcyclopropan 
• 1499-63-4 (2S*,3R*)-3-methyl-4-phenyl-2-butanol 
• 125830-08-2 (2R*,3R*)-2-methoxy-3-methyl-4-phenylbutane 
• 125830-10-6 (2R*,3R*)-2,3-dimethyl-4-phenylbutanecarbonitrile 
• 1499-63-4 (2R*,3R*)-3-methyl-4-phenyl-2-butanol 

Relevant academic research and scientific papers

THE STEREOCHEMISTRY OF ATTACK BY A CARBON ELECTROPHILE ON A TIN-CARBON BOND

In the cyclisation of the 5-stannyl aldehyde (3), the cyclopentanol ring (4) is formed with retention of configuration at the carbon * bearing the stannyl group.

Three-electron S(N)2 reactions of arylcyclopropane cation radicals. 1. Mechanism

The mechanism of photosensitized nucleophilic substitution reactions on arylcyclopropanes was investigated. Stereochemical experiments with methanol, water, and cyanide as nucleophiles showed that the reactions occurred stereospecifically with complete inversion of configuration at the carbon atom undergoing substitution. Independent generation of the arylcyclopropane cation radicals by nanosecond transient methods showed that they reacted rapidly with nucleophiles with kinetics that were first-order in both the cation radical and the nucleophiles. Through a combination of transient kinetics and steady-state Stern-Volmer quenching experiments, the reaction of the phenylcyclopropane cation radical with methanol was kinetically correlated with the formation of the substitution product. The reaction of phenylcyclopropane cation radical with a series of alcohols as nucleophiles showed small steric effects.

THE STEREOCHEMISTRY OF THE INTRAMOLECULAR ELECTROPHILIC ATTACK OF AN ALDEHYDE ON A CARBON-TIN BOND

The cyclopentane-forming reaction (20-43) of (4RS,5SR)-2,2,4-trimethyl-5-trimetstannylhexanal takes place with retention of configuration at the carbon atom undergoing electrophilic substitution, in contrast to similar cyclopropane-forming reactions (e.g. 47-48), which take place with inversion of configuration.The hydride transfer (24-45) of the 4RS,5RS diastereoisomeric hexanal takes place from a conformation with hydride anti to the stannyl group.In the case of reacions which might have formed four-membered rings, fragmentation takes place (16-28 and 17-30).The presence of a phenyl ring on the carbon carrying the stannyl group interferes with the reactions designed to test the stereochemistry of the SE2 reaction, diverting the reaction to the formation of tetralins (10-26 and 34-38) or benzcycloheptenes (34-37).

Regioselectivity in the Addition of Singlet and Triplet Carbenes to 1,1-Dimethylallene. A Probe for Carbene Multiplicity

Singlet carbenes add preferentially to the more substituted bond of 1,1-dimethylallene (1), to give methylenecyclopropanes 3 as the major product.In contrast, many triplet carbenes add with differing regioselectivity, giving the thermodynamically preferre