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Extra resources for Chemistry of Heterocyclic Compounds: The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth, Volume 1
The probable mechanism of this hydrolysis supports the earlier thesis that the presence of a small ring, which prefers the equatorialapical 90' bond angle to the diequatorial 120" angle in a trigonalbipyramidal intermediate, can direct the course of the subsequent reaction. p. , 1,2,3,4-tetrahydro-1 ,2,2,3,4,4-hexamethylphosphinolirie 1-oxide (cf. I,. 124). p. p. 108-120" (81%). * 12 Part I Cremer ‘Ja has later reinvestigated the alkaline hydrolysis of 1,2,2,3,4,&hexamethyl-1 -phenylphosphetanium bromide, and by deuterium labelling has reaffirmed the formation of the phosphine oxide (18): rearrangement of this oxide t o the substituted phosphinoline oxide (29) presumably occurs during the aromatization process in boiling decalin.
These workers showed that the dilithio derivative (3)when treated with iodine, both in ethereal solution, deposited 1,4-diiodo-1,2,3,4-tetraphenylbutadiene, C6H,C(I)==C(C6H5)-C(C6H5)=C(I)C6H5, map. 202", and that this compound would condense with many compounds of type R,MX2, where R is an alkyl or aryl group, M is the heteroatom, and X a univalent element, to give the corresponding five-membered ring: for example, the diiodo compound condensed with phenyldisodiophosphine, to give pentaphenylphosphole (4; R = C6H5),thus providing a third synthetic route.
C) When added to an excess of ice, the compound (9) gives avigorous reaction and ultimately a clear solutioii, which on removal of the water leaves the residual crude 1 -hydroxy-2-pho~phoIeneI-oxide (14)in almost theoretical yield. s 95-97" and 69-70'. (d) Compounds of type (15). (16),and (17) are all obtained by treating (9) with ethancthiol under various conditions. A solution of (9) in dry dichloromethane, treated with the thiol (1 mole) at room temperature and distilled after several houra, gives the I-chloro 1-sulfide(15).
Chemistry of Heterocyclic Compounds: The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth, Volume 1