CYCLOPROPYL PHENYL SULFIDE

CLEAR YELLOWISH LIQUID

Cyclopropyl phenyl sulfide was used as a reagent in the conversion of a ketone into a spirocyclobutanone.

Synthetic Communications, 10, p. 311, 1980 DOI: 10.1080/00397918008062755

Phenylthiocyclopropane is easily prepared from 1-phenylthio-3-chloropropane (itself obtained on reaction of 1-bromo- 3-chloropropane and phenylthiolates) and Potassium Amide in liquid ammonia (eq 1).

1,3-Bis(phenylthio)propane reacts with n-Butyllithium in THF to produce Phenylthiocyclopropane on reaction with only 1 equiv n-Buli, or 1-lithio-1-phenylthiocyclopropane (2) if 2 equiv are used (eq 2).
Phenylthiocyclopropane has also been synthesized from 3-tributylstannylpropanal (available from tributylstannyllithium and Acrolein) and trimethylsilyl phenyl sulfide in the presence of Titanium(IV) Chloride as acid catalyst (eq 3), and on substitution of (i) Cyclopropyllithium with Diphenyl Disulfide (eq 4), (ii) cyclopropyl bromide with potassium benzenethiolate (eq 5) or (iii) 1,1-dibromocyclopropane, also with benzenethiolates, and by reduction of α- bromocyclopropyl phenyl sulfide with sodium methanethiolate (eq 6). In addition, cyclopropyl phenyl sulfoxide can be reduced to (1) in more than 70% yield with Chlorotrimethylstannane-benzenethiol (eq 7).