267668-24-6

Basic information

• Product Name: N-tert-butyloxycarbonyl-N-(1-hydroxymethyl-2-propenyl)benzenesulfenamide
• Synonyms: N-tert-butyloxycarbonyl-N-(1-hydroxymethyl-2-propenyl)benzenesulfenamide
• CAS NO: 267668-24-6
• Molecular Weight: 295.403
• Mol File: 267668-24-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-tert-butyloxycarbonyl-N-(1-hydroxymethyl-2-propenyl)benzenesulfenamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-butyloxycarbonyl-N-(1-hydroxymethyl-2-propenyl)benzenesulfenamide(267668-24-6)
• EPA Substance Registry System: N-tert-butyloxycarbonyl-N-(1-hydroxymethyl-2-propenyl)benzenesulfenamide(267668-24-6)

Safety Data

• Hazardous Substances Data: 267668-24-6(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 52938-71-3 (E)-3-methoxycarbonylprop-2-enyl phenyl sulfide 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 121666-84-0 (E)-4-hydroxy-2-butenyl phenyl sulfide 

Downstream Products

• 169324-82-7 N-tert-butoxycarbonyl-N-(1-hydroxymethyl-2-propenyl)amine 

Relevant articles and documents

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).