Reactions of 2,4,6-Tri-t-butylphenyllithium with Deuterated Formate, Thioformate and Selenoformate

Article abstract of DOI:10.1246/bcsj.60.1037

O-Cholesteryl chalcogenoformates-d, DC(=X)(OR) (2: X=O; 3: X=S; 4: X=Se; R=3β-cholesteryl), were synthesized and allowed to react with 2,4,6-tri-t-butylphenyllithium. 1,3,5-Tri-t-butylbenzene was a main product in each reaction. The other products were 2,4,6-tri-t-butylbenzaldehyde-d (9) for 2, 2,4,6-tri-t-butylthiobenzaldehyde-d for 3, and 9, 6,8-di-t-butyl-1-deuterio-3,4-dihydro-4,4-dimethyl-1H-2-benzoselenin, bis(2,4,6-tri-t-butyl-α-deuteriobenzyl) diselenide, and bis(2,4,6-tri-t-butyl-α-deuteriobenzyl) triselenide for 4.The mechanisms for these reactions have been discussed.