7559-34-4

Upstream product

• 823-94-9 2,4,6-trimethyl-s-triazine 
• 74-96-4 ethyl bromide 
• 138606-51-6 1-(4,6-dimethyl-s-triazin-2-yl)-1-propene 
• 280-64-8 9-bora-bicyclo[3.3.1]nonane 

Relevant academic research and scientific papers

Hydration with mercuric acetate and the reduction with 9-BBN-H of 2-(1-alkenyl)-4,6-dimethyl-s-triazines

Oxymercuration-demercuration of a double bond in conjugation with the 4,6-dimethyl-s-triazin-2-yl substituent as in alkenes la,b gave anti-Markovnikov regioselectivity, which is explained by the electron-withdrawing nature of the triazinyl substituent. However, hydroboration of the conjugated alkenes with 9-BBN-H gave the corresponding alkenes 5a-c under normal workup conditions with or without oxidation. With time and without workup the hydroboration of 1b gave spectral evidence for the formation of intermediates 9-13 resulting from the migration of the 9-BBN moiety from the α-carbon to a ring nitrogen with concurrent formation of an exocyclic double bond to an α-carbon of the ring. Hydrolysis of the intermediates gave 5a-c. A possible mechanism involving successive allylic rearrangements is presented.