1993
DOI: 10.1002/hc.520040227
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A new rearrangement in phosphorus chemistry

Abstract: The oxidation of 1,5-dimethy2-2,4-bis(diethylamino)-I,5-diaza-2,4-diphosphorinan-6-one 5 with tetrachloroorthobenzoquinone (TOB) leads to the formation of the spirophosphorane 9, which is unstable and undergoes an unusual spontaneous rearrangement into the isomeric methylenephosphinophosphorane 1 1. The sulfuration of 9 a.nd 11 gives the stable isomers 12 and 19, exhibiting no tendency of mutual transformation. The mechanism of the isomerization of 9 into 11 is discussed. Some chemical properties of 9 and 11 h… Show more

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Cited by 6 publications
(8 citation statements)
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“…128, 129 The X-ray crystal structure of 77 ( Figure 39) 128 shows a distorted octahedral six-coordinate phosphorus center possessing three chelates of ring sizes four, five, and seven. The major distortions derive from the strained four-membered ring.…”
Section: Three Bidentate Chelatesmentioning
confidence: 99%
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“…128, 129 The X-ray crystal structure of 77 ( Figure 39) 128 shows a distorted octahedral six-coordinate phosphorus center possessing three chelates of ring sizes four, five, and seven. The major distortions derive from the strained four-membered ring.…”
Section: Three Bidentate Chelatesmentioning
confidence: 99%
“…The P-N bond lengths are relatively long (3.01 Å) but are shorter than the sum of van der Waals radii. 126 Recently, Shevchenko and Schmutzler [127][128][129][130] have reported detailed studies of 1,3-diaza-4,6-diphosphorines (71a,b, Figure 35) with tetrachloroorthobenzo-quinone. It has already been noted that the subtle change in steric behavior between 71a and 71b has produced significant differences in their chemical behavior.…”
Section: Three Bidentate Chelatesmentioning
confidence: 99%
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