267668-39-3

Basic information

• Product Name: Carbamic acid, (1,2-dimethyl-2-propenyl)-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, (1,2-dimethyl-2-propenyl)-, 1,1-dimethylethyl ester (9CI);(1,2-Dimethyl-allyl)-carbamic acid tert-butyl ester
• CAS NO: 267668-39-3
• Molecular Formula: C10H19NO2
• Molecular Weight: 185.26336
• Product Categories: N-BOC
• Mol File: 267668-39-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, (1,2-dimethyl-2-propenyl)-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (1,2-dimethyl-2-propenyl)-, 1,1-dimethylethyl ester (9CI)(267668-39-3)
• EPA Substance Registry System: Carbamic acid, (1,2-dimethyl-2-propenyl)-, 1,1-dimethylethyl ester (9CI)(267668-39-3)

Safety Data

• Hazardous Substances Data: 267668-39-3(Hazardous Substances Data)

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 267668-29-1 N-tert-butyloxycarbonyl-N-(1,2-dimethyl-2-propenyl)benzenesulfenamide 

Relevant articles and documents

Access to enantiomerically enriched cis-2,3-disubstituted azetidines via diastereoselective hydrozirconation

An asymmetric variant of the hydrozirconation reaction has been established starting from Boc-protected chiral allylic amines. The resulting diastereoselectively formed N-functionalized organozirconiums can be considered as promising chirons. In this case

Fe(II)-catalyzed imidation of allyl sulfides and subsequent [2,3]- sigmatropic rearrangement. Preparation of α-branched N-tert-butyloxycarbonyl (Boc)-protected N-allylamines

Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2,3]- sigmatropic rearrangement reaction upon treatment with N-tert- butyloxycarbonyl azide (BocN3) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75% (12 examples). Whereas the reaction is well suited for the transformation of α-unbranched sulfides to α-branched sulfenamides, the enantiomerically pure α-branched sulfides 10 and 13 reacted sluggishly. The corresponding sulfenamides 22 and 23 were obtained in only moderate enantiomeric excess (36-39% ee). A reaction mechanism is proposed that postulates the intermediacy of an N-Boc-substituted Fe(IV)-nitrene complex 14 acting as the imidation reagent in the catalytic cycle. Possible side reactions are discussed. The benzenesulfenamides 3 were further converted into N-Boc-N-allylamines 4 by removal of the phenylsulfanyl group. Bu3SnH in benzene was found to be the reagent of choice for the deprotection of α- branched amines that bear a secondary allyl substituent (five examples, 71- 93% yield). This method failed for the α-branched amines 3i-k with a tertiary allyl substituent. The phenylsulfanyl group was finally removed with P(OEt)3/NEt3 in CH2Cl2 (three examples, 43-62% yield).