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2,4,8,10‐Tetraoxa‐3,9‐diphosphaspiro[5.5]undecane‐3,9‐disulfide and Some Derived Compounds
Author(s) -
Rätz Rudi,
Bliss Arthur D.
Publication year - 1966
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570030104
Subject(s) - undecane , chemistry , disulfide bond , hydrogen sulfide , sulfide , yield (engineering) , medicinal chemistry , carbon disulfide , carbonyl sulfide , organic chemistry , sulfur , biochemistry , materials science , metallurgy
2,4,8,10‐Tetraoxa‐3,9‐diphosphaspiro[5.5]undecane‐3,9‐disulfide (I) has been prepared by the treatment of 3, 9‐dichloro‐2,4,8,10‐tetraoxa‐3,9‐diphosphaspiro[5.5]undecane (II) with hydrogen sulfide. The reactions of I with thiocyanates to give esters of 3,9‐dimercapto‐2,4,8,10‐tetraoxa‐3,9‐diphosphaspiro[5.5]undecane‐3, 9‐disulfide (III) and with isocyanates and isothiocyanates to give P ‐carbamoyl and thiocarbamoyl derivatives of I were investigated. I was also found to condense with chloral to produce an α‐hydroxy‐thiophosphonate (XXVIII), but similar reactions with other aldehydes failed to yield analogous products.