New 7‐phosphanorbornenes derived from 2‐methyl‐1‐phenyl‐ and 1‐cyclohexyl‐3‐ methyl‐2,5‐dihydro‐1H‐phosphole 1‐oxides

Abstract

Novel 7-phosphanorbornene derivatives, such as 4, 5, 10, and 11 were synthesized utilizing 1-phenyl-2-methyl-2,5-dihydro-1H-phosphole oxide (1) and 1-cyclohexyl-3-methyl-2,5-dihydro-1H-phosphole

A study on the ability of 2,5‐dihydro‐ and 2,3,4,5‐tetrahydro‐1h‐phosphole oxides, as well as 7‐phosphanorbornene 7‐oxide derivatives to undergo uv light‐mediated fragmentation‐related phosphinylation of methanol

“…1-Benzyl-2,5-dihydro-1H-phosphole oxide 4 was synthesized by the method applied for the preparation of 2 [14]. The 13 C NMR spectral data of 4 were identical with those described in the literature [17].…”

“…10 -5 mol·l -1 acetonitrile solutions. The 3-methyl-2,5-dihydro-and 2,3,4,5-tetrahydro-1H-phosphole oxides (2 [14], 3 [15], 5 [16] and 6 [16]), as well as the 7-phosphanorbornene 7-oxides (7-10) [14] were prepared as described earlier. P-cycles 5 and 6 were used as ca.…”

“…Figure 1 shows the variety of P-heterocycles (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) studied in fragmentation-related phosphinylations. As can be seen, the precursors include 2,5-dihydro-1H-phosphole oxides (1-5), a 2,3,4,5-tetrahydrophosphole oxide (6) and 7-phosphanorbornene oxides, such as the dimers of 1H-phosphole oxides (7, 9, 11 and 13), as well as the cycloadducts of 1H-phosphole oxides with N-phenylmaleimide (8, 10, 12 and 14).…”

“…Bridged P-heterocycles 7-14 were prepared by well-established general methods [8]. A part of the 7-phosphanorbornene 7-oxides (11)(12)(13)(14) are new whose synthesis is shown in Scheme I. It can be seen that the 2,5-dihydro-1H-phosphole oxides (3 or 4) were converted to dibromo-tetrahydrophosphole oxides 15 and 16 giving phosphole oxides 17 and 18 by double dehydrobromination.…”

A new P‐heterocyclic family: A variety of six‐membered and bridged P‐heterocycles with 1‐benzyl substituent

“…The intermediates of the above P-heterocycles are the suitably substituted 2,5-dihydro-1H-phosphole 1-oxides available easily. The 1-benzyl-P-heterocycles form a relatively less studied group; only simple derivatives, SCHEME 1 such as the corresponding 1H-phosphole [7], 2,5-dihydro-and 2,3,4,5-tetrahydro-1H-phosphole oxides [8,9], as well as some other species including 7-phosphanorbornene 7-oxides [10] have been described. In this paper, the 1-benzyl derivatives of a variety of six-membered P-heterocycles, mainly phosphinines, as well as bridged P-heterocycles, such as phosphabicyclooctenes, are discussed.…”