Advances in Strained and Interesting Organic Molecules, by B. Halton

By B. Halton

The 8th quantity of this sequence includes six chapters and describes a number of attention-grabbing strained and never so strained molecules and their use - or abuse - within the widest feel. This quantity encompasses a place precis of planar carbon networks, the sector of strained allenesis addressed via contemplating the 5- to- nine-membered ring derivatives and this can be by means of an creation to the character of carbene geometry and using ESR spectroscopy in deducing carbene constitution. using strained molecules within the synthesis of significant new compounds of a ordinary and non-natural nature is a major topic within the quantity. different components which are mentioned are strained carbohydrates, stereocontrolled entry to traditional items and polymer platforms in addition to a far wanted contribution to the sequence on small-ring nitrogen heterocycles.

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I . 25% Me~3~S s~ ild~ d,f,j _ ~t2 14% p~ Scheme 17. Reagents:(a) BnEt3N+ICI~, CaCO3, CH2CI2, MeOH; (b)i] NaNO2, HCI, MeCN, H20, ii] Et2NH, K2CO3, H20; (c) Me3SiC~CH, PdCI2(PPh3)2,Cul, Et3N; (d) Mel, 120 ~ (e) i-Pr3SiC~CH, PdCI2(PPh3)2,Cul, Et3N; (f) K2CO3, THF, MeOH; (g) N,N-Diethyl-o-ioclophenyltriazene, PdCI2(PPh3)2,Cul, Et3N; (h) Bu4N+F-, THF, EtOH; (i) 87, PdCI2(PPh3)2,Cul, Et3N; (j) Pd(dba)2, PPh3, Cul, Et3N. 24 MICHAEL M. HALEY and W. BRAD WAN (BnNEt3)+IC1] [60] provided 2,6-diiodo-4-tert-butylaniline in high yield under mild conditions.

1 Hexabutadiynylbenzenes Building on their earlier success, the Vollhardt group reported the preparation of three hexabutadiynylbenzene derivatives 90 in 1992 [62]. Again starting with hexabromobenzene, Sonogashira coupling provided the molecules in low to modest yield. Attempts to prepare the parent hydrocarbon by protiodesilylation failed due to its instability. A more "advanced" graphdiyne model (91) was recently synthesized from hexaiodobenzene and p-t-butylphenylbutadiyne in 42% yield using the highly reactive catalyst Pd[P(o-tol)3]2 [63].

57] Bradshaw, J. , Tessier, C. , and Youngs, W. , J. Am. Chem. , 116 (1994) 3177. [58] Haley, M. , Kehoe, J. , and Kiley, J. , submitted. [59] Moore, J. , Weinstein, E. , and Wu, Z. , 32 (1991) 2465. , Bull. Chem. Soc. , 61 (1988) 118. , Phys. Rev. B, 58 (1998) 11009. , Green, J. , Molder, D. , and Vollhardt, K. , Angew. , Int. Ed. , 31 (1992) 1643. [63] Wan, W. B. and Haley, M. , unpublished results. [64] Eglinton, G. and Galbraith, A. , Proc. Chem. , (1957) 350; Behr, O. , and Raphael, R. , Chem.

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