1415046-74-0

Basic information

• Product Name: C₂₃H₃₂N₂O₃S
• Synonyms: C₂₃H₃₂N₂O₃S
• CAS NO: 1415046-74-0
• Molecular Weight: 416.585
• Mol File: 1415046-74-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₃H₃₂N₂O₃S(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₃H₃₂N₂O₃S(1415046-74-0)
• EPA Substance Registry System: C₂₃H₃₂N₂O₃S(1415046-74-0)

Safety Data

• Hazardous Substances Data: 1415046-74-0(Hazardous Substances Data)

Upstream product

• 109-74-0 propyl cyanide 
• 3608-11-5 4-α-acetyl-2-carene 
• 127-65-1 chloroamine-T 

Relevant articles and documents

Bromenium-catalysed tandem ring opening/cyclisation of vinylcyclopropanes and vinylcyclobutanes: A metal-free [3+2+1]/[4+2+1] cascade for the synthesis of chiral amidines and computational investigation

We present a detailed study of a [3+2+1] cascade cyclisation of vinylcyclopropanes (VCP) catalysed by a bromenium species (Br δ+-Xδ-) generated in situ, which results in the synthesis of chiral bicyclic amidines in a tandem one-pot operation. The formation of amidines involves the ring-opening of VCPs with Br-X, followed by a Ritter-type reaction with chloramine-T and a tandem cyclisation. The reaction has been further extended to vinylcyclobutane systems and involves a [4+2+1] cascade cyclisation with the same reagents. The versatility of the methodology has been demonstrated by careful choice of VCPs and VCBs to yield bicyclo[4.3.0]-, -[4.3.1]- and -[4.4.0]amidines in enantiomerically pure form. On the basis of the experimental observations and DFT calculations, a reasonable mechanism has been put forth to account for the formation of the products and the observed stereoselectivity. We propose the existence of a π-stabilised homoallylic carbocation at the cyclopropane carbon as the reason for high stereoselectivity. DFT studies at B3LYP/6-311+G** and M06-2X/6-31+G* levels of theory in gas-phase calculations suggest the ring-opening of VCP is initiated at the π-complex stage (between the double bond and Br-X). This can be clearly perceived from the solution-phase (acetonitrile) calculations using the polarisable continuum model (PCM) solvation model, from which the extent of the ring opening of VCP was found to be noticeably high. Studies also show that the formation of zero-bridge bicyclic amidines is favoured over other bridged bicyclic amidines. The energetics of competing reaction pathways is compared to explain the product selectivity. Copyright