932-56-9

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 30, p. 119, 1982 DOI: 10.1248/cpb.30.119

Upstream product

• 931-66-8 1-methylcycloheptene 
• 329971-04-2 cyclooctylidene-(3-methyl-pyridin-2-yl)-amine 
• 50338-48-2 1-Trimethylsiloxy-bicyclo[5.1.0]octan 
• 74067-02-0 (+/-)-2t-chloro-1r-methyl-cycloheptanol-⁽¹⁾ 
• 7732-18-5 water 
• 168482-48-2 2-(1-trimethylstannylethyl)-1-cyclohexanone 
• 110977-08-7 (1RS,2SR)-(4-tert-butyl-2-methyl-2-phenylthiocycloheptyl)toluene-p-sulfonate 
• 2658-60-8 1,1-bis(hydroxymethyl)cyclohexane 

Downstream Products

• 20053-89-8 1,2-Dimethyl-cyclohepten 
• 14112-98-2 7-oxooctanoic acid 
• 35125-29-2 3-methyl-cycloheptane-1,2-dione 
• 13151-51-4 cis-1,2-Dimethyl-cycloheptan 
• 13151-50-3 trans-1,2-Dimethylcycloheptan 
• 33015-78-0 N-(2-Methylcycloheptyliden)anilin 
• 117543-18-7 2-Methyl-1-(nitro-phenylsulfanyl-methyl)-cycloheptanol 
• 135940-21-5 [2-Methyl-cyclohept-(Z)-ylidene]-((S)-1-phenyl-ethyl)-amine 
• 135940-21-5 [2-Methyl-cyclohept-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 
• 135971-94-7 (αS,1S,2R)-(-)-cis-2-Methyl-N-(1-phenylethyl)cycloheptanamin-Hydrochlorid 
• 135940-21-5 [2-Methyl-cyclohept-(Z)-ylidene]-((R)-1-phenyl-ethyl)-amine 
• 135940-21-5 [2-Methyl-cyclohept-(E)-ylidene]-((R)-1-phenyl-ethyl)-amine 
• 136030-05-2 (αR,1R,2S)-(+)-cis-2-Methyl-N-(1-phenylethyl)cycloheptanamin-Hydrochlorid 
• 812639-05-7 allyl 2-methylcyclohept-1-enyl carbonate 

Relevant academic research and scientific papers

Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to β-keto radicals

Siloxy cyclopropanes undergo ring opening and fragmentation of formal silyl cations under formation of β-keto radicals. These reactive intermediates can be used in inter- and intramolecular addition reactions leading to complex ring systems if more than one unsaturated side chain is present in the starting material. Beside some synthetic examples mainly the mechanism will be discussed focusing on the structure of the primarily formed radical cations, the regioselectivity of cyclopropane cleavage (endo vs exo ring opening), leaving of the silyl group, and termination by H-transfer.

Ring enlargement of α-ethylidenecycloalkanones to β-alkylidenecycloalkanones induced by trimethylstannyllithium/aldehyde equivalents/Lewis acids

α-Ethylidenecycloalkanones underwent a ring enlargement to β-alkylidenecycloalkanones upon a treatment with trimethylstannyllithium/aldehyde equivalents/Lewis acids with high stereoselectivity.

Alkyl Migration in Competition with Phenylthio Migration in the Acid-catalysed Rearrangement of Alcohols

Sulfonate derivatives of conformationally rigid syn-2-phenylthiocyclohexanols, which are prevented from phenylthio migration by stereochemistry, rearrange slowly by alkyl migration or ring contraction.In contrast to other electronegative groups, phenylthio slows the reaction down but allows migration of other groups.

Studies on the chemistry of diols and cyclic ethers-53. Dehydration of 1,1-bishydroxymethylcycloalkanes: A quest for a 1,3-hydride shift

A study of the sulphuric acid-catalysed dehydrations of 1,1-bishydroxymethyl-cyclopropane, - cyclobutane, - cyclopentane and -cyclohexane (1a-1d) revealed that the product distributions are determined by the relative stabilities of carbenium ions and der kinetic control furnished evidence of a 1,3-hydride shift.

ALKYL MIGRATION INCLUDING RING CONTRACTION FROM A MIGRATION ORIGIN BEARING A PHENYLTHIO (PhS) GROUP

Alkyl shifts occur from tertary C atoms bearing a PhS group if PhS migration is prevented, but are retarded by the PhS group: the transition state has a cation-like migration terminus with little, if any, alkyl participation.

LIGHT-MEDIATED TRANSFORMATIONS OF OLEFINS INTO ALCOHOLS: REACTIONS OF HYDROXYL RADICALS WITH CYCLOALKENES

Reactions of hydroxyl radicals, generated by photodecomposition of hydrogen peroxide in acetonitrile, with a wide variety of cycloalkenes have been examined.The results show that the major reaction is the addition of hydroxyl radicals to the less substituted end of the double bond, furnishing the secondary alcohols.The reactivity pattern and the observed regio- and stereoselectivity clearly reveal that the steric parameters associated with the substrates play a dominant role in directing the addition reactions.More importantly, this study led to the development of a new methodology for the facile conversions of olefins essentially into secondary alcohols, and includes a few examples which demonstrate the potential of the method.