136742-92-2

Upstream product

• 56-23-5 tetrachloromethane 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 95189-55-2 3,4,5,7-Tetra-O-benzyl-2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptitol 

Relevant academic research and scientific papers

Dichloromethylenation of Lactones. 6. Efficient Synthesis of Dichloroolefins from Lactones and Acetates Using Triphenylphosphine and Tetrachloromethane

Triphenylphosphine and tetrachloromethane react cleanly in refluxing tetrahydrofuran with substituted γ- and δ-lactones and some esters to afford the corresponding dichloroolefins in good yields.This new Wittig-type reaction provides an easy entry to this new class of compounds and tolerates a large of protecting groups.Application of this methodology to the dichloroolefination of simple lactones, suger-derived lactones, and other biologically significant lactones is described.

Unusual Behaviour of Some γ- and δ-Lactones Towards Dichloromethylenation using Tris(dimethylamino)phosphine-Tetrachloromethane

Lactones derived from D-glucose, D-mannose and L-ascorbic acid reacted unexpectedly with tris(dimethylamino)phosphine-tetrachloromethane to give, respectively, dichloroalkene, anomeric vinyl chloride or acyl chloride; this behaviour supports an ionic mech