Synthesis of selectively deuterated fulvenes and indenes from enediynes

Abstract

A facile enediyne--> fulvene--> indene transformation provides a route to all possible isotopomers of substituted fulvenes and indenes.

Recent Advances in the Synthesis of Indanes and Indenes

“…In another approach, the indenyllithium intermediates 381 were obtained by addition of BuLi or LiAlH 4 to ( E )‐1‐benzylidene‐2‐phenyl‐1 H ‐indene 380 . The subsequent quenching with D 3 O + allowed an easy synthesis of deuterated indenes 382 (Scheme ) . 2‐Lithioindenyllithium 384 , obtained by dilithiation of 2‐bromoindene 383 , was also used for the preparation of deuterated indenes and silicon‐bridged bisindenyl derivatives, as exemplified in Scheme for the preparation of 385 …”

“… Synthesis of deuterated indenes 382 by addition of BuLi or LiAlH 4 to ( E )‐1‐benzylidene‐2‐phenyl‐1 H ‐indene 380 followed by quenching with D 3 O + …”

10.1007/s11176-008-2012-z

“…Addition of Bu 3 Sn . With a view to elucidate the reaction mechanism, fulvenes were subjected to selective deuteration [62] (Scheme 26). Reactions of enediynes with radical reagents were studied in part previously [48,60,61].…”

Synthesis of new organophosphorus‐substituted fulvenes with indenyl moieties

“…At the same time, the stable substituted 6‐dimethylaminofulvene was obtained in high yield based on cyclopentadiene and dimethylformamide [6]. The original synthesis of substituted fulvenes is associated with the radical cyclization of substituted o ‐phenylenediynes in the presence of tributyltin hydride [7]. Preliminary brief data on the synthesis of organophosphorus benzofulvenes were published by us earlier (cf [8a]…”