17553-36-5

Basic information

• Product Name: trans-tert-butyl(4-²H₁)cyclohexane
• Synonyms: trans-tert-butyl(4-²H₁)cyclohexane
• CAS NO: 17553-36-5
• Molecular Weight: 141.261
• Mol File: 17553-36-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: trans-tert-butyl(4-²H₁)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: trans-tert-butyl(4-²H₁)cyclohexane(17553-36-5)
• EPA Substance Registry System: trans-tert-butyl(4-²H₁)cyclohexane(17553-36-5)

Safety Data

• Hazardous Substances Data: 17553-36-5(Hazardous Substances Data)

Upstream product

• 937-05-3 cis-4-tert-butyl-1-cyclohexanol 
• 21862-63-5 trans-4-tert-butylcyclohexanol 
• 599-00-8 trifluoroacetic acid-d₁ 
• 16133-41-8 cis-1-(tert-butyl)-4-iodocyclohexane 
• 85592-89-8 1-(tert-butyl)-4-iodocyclohexane 
• 53042-75-4 trans-4-tert-butyl-<1-(2)H>-<(p-tolylsulfonyl)oxy>cyclohexane 
• 5009-36-9 cis-1-bromo-4-tert-butylcyclohexane 
• 7080-86-6 1-(tert-butyl)-4-bromocyclohexane 
• 62056-46-6 4-tert-butyl-1-chlorocyclohexane 
• 7453-05-6 toluene-4-sulfonic acid-(trans-4-tert-butyl-cyclohexyl ester) 

Relevant articles and documents

Deuterium and Tritium Labeling with the Zinc-Sodium Iodide Method

Primary and secondary hydroxyl groups can be replaced by deuterium or tritium when the corresponding sulfonate esters are reduced with zinc, sodium iodide, and deuterium or tritium oxide in 1,2-dimethoxyethane.The method tolerates a variety of other reducible functionalities, namely, α,β-enone, ketone, and ester.The labeling can be conducted with a high regiospecificity in the presence of enolizable hydrogens.The method is less satisfactory for a stereospecific replacement of secondary hydroxyl groups, yielding mixtures of stereoisomers and olefins as byproducts.The distribution of the stereoisomers depends on the rate of configurational inversion in the intermediary iodides arising by displacement of the original tosyloxy group.Deuterium NMR spectra and their use in the configurational assignment are discussed.

Stereoselective Retentive Domino Transmetalations of Secondary Alkyllithium Compounds to Functionalized Secondary Alkylcopper Reagents

Functionalized secondary alkyllithium reagents obtained by I/Li exchange from the corresponding secondary alkyl iodides undergo two successive transmetalations with Me3SiCH2ZnBr.LiBr and CuBr.2LiCl.Me2S to provide functionalized secondary alkylcopper compounds with high retention of configuration. These alkylcopper derivatives react further with electrophiles such as alkynyl esters, acid chlorides, allylic chlorides, ketals, ethylene oxide, and 3-iodocyclopentanone with high retention of configuration. A related sequence of transmetalations with MeMgI and LaCl3.2LiCl allows a retentive addition of secondary alkyllithium reagents to acetone. The influence of the solvent on the configurational stability of secondary alkylzinc reagents is described.

Preparation and reactivity of chiral β-amino-alkylzinc iodides and related configurationally stable zinc organometallics

Several zinc organometallics bearing at the β-position a carbamate or an amido function with an acidic N-H group were prepared using the direct insertion of zinc dust into the corresponding alkyl iodides in THF or THF:DMSO mixtures. Most of the starting iodides were obtained from natural α-amino acids and the resulting zinc species afforded after transmetalation with CuCN.2LiCl and reaction with a selection of relatively reactive electrophiles a variety of polyfunctional 1,2-amino alcohol derivatives and carbamates in optically pure form. Several secondary β-amido alkyl iodides were converted to the corresponding chiral zinc reagents and trapped with electrophiles. The configurational stability of chiral secondary organozinc compounds and the stereochemical course of their reactions were examined.