910-31-6Relevant articles and documents
Regioselective opening of a cyclopropane ring by mercury(II) and transmetalation of the product with molybdenum. A novel, stereoelectronically controlled, skeletal rearrangement ans Grob-type fragmentation of organomolybdenum intermediates
Srogl, Jiri,Kocovsky, Pavel
, p. 5991 - 5994 (1992)
Organomercurial 2, arising by a regioselective ring-opening of cyclopropane derivative 1, can be transmetalated with Mo-reagents to initially generate complexes 3 and 7. While 3 reacts further via a stereoelectronically controlled cascade rearrangement to afford 6, complex 7 favors a Grob-type fragmentation leading to 9.
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Heilbron,Samant,Simpson
, p. 1410,1412 (1933)
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Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors
Wu, Xiangyu,Hao, Wei,Ye, Ke-Yin,Jiang, Binyang,Pombar, Gisselle,Song, Zhidong,Lin, Song
supporting information, p. 14836 - 14843 (2018/11/10)
Alkyl chlorides are common functional groups in synthetic organic chemistry. However, the engagement of unactivated alkyl chlorides, especially tertiary alkyl chlorides, in transition-metal-catalyzed C-C bond formation remains challenging. Herein, we describe the development of a TiIII-catalyzed radical addition of 2° and 3° alkyl chlorides to electron-deficient alkenes. Mechanistic data are consistent with inner-sphere activation of the C-Cl bond featuring TiIII-mediated Cl atom abstraction. Evidence suggests that the active TiIII catalyst is generated from the TiIV precursor in a Lewis-acid-assisted electron transfer process.
Dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1: H,1′ H-4,4′-bipyridinylidene for giving alkenes and alkynes in a salt-free manner
Rej, Supriya,Pramanik, Suman,Tsurugi, Hayato,Mashima, Kazushi
supporting information, p. 13157 - 13160 (2017/12/26)
We report a transition metal-free dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1H,1′H-4,4′-bipyridinylidene (1) under mild conditions, in which trimethylsilyl halide and 4,4′-bipyridine were generated as byproducts. The synthetic protocol for this dehalogenation reaction was effective for a wide scope of dibromo compounds as substrates while keeping the various functional groups intact. Furthermore, the reduction of vicinal dichloro alkanes and vicinal dibromo alkenes also proceeded in a salt-free manner to afford the corresponding alkenes and alkynes.
